


Dangerous Daddy

by Lis



Category: Supernatural
Genre: Abusive Relationships, Alternate Universe, Blood, Bloodplay, Daddy Kink, Dildos, Evil Dean, Evil Dean Winchester, F/M, Forced Relationship, Gang Violence, Gangs, Gun Violence, Knifeplay, M/M, Manipulation, Multi, Murder, Nipple Clamps, Nipple Play, Obsessive Behavior, Organized Crime, Possessive Behavior, Possessive Dean, Rape/Non-con Elements, Rough Sex, Sexual Abuse, Spanking, Torture, Violence
Language: English
Status: In-Progress
Published: 2017-05-02
Updated: 2018-03-24
Packaged: 2018-10-26 20:10:53
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con, Underage
Chapters: 23
Words: 26,314
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10793907
Author URL: https://archiveofourown.org/users/Lis/pseuds/Lis
Summary: Dean Winchester is the leader of a gang called the Devils. He's dangerous and loves causing pain and terror. He meets Lisa Holland by chance one day. She's innocent, naive, and not that interested in him. He becomes obsessed and abusive. She is oblivious to his gang affiliation at first and doesn't realize how far Dean is willing to go to keep her.The smut is terrible, so it's not in every chapter.Please comment suggestions and critiques.





	1. Intro

**Author's Note:**

> Comments give me life, please let me know if you like it or hate it or have storyline suggestions. I'm making this up as I go.

Dean Winchester was a man of little patience. He grew up the eldest son of John Winchester, an immensely rich and powerful man. His father was the head of one of the largest gangs in America, running the city of LA. The Devils, which he jokingly named when he was six-teen not knowing it would stick for life, was his pride and joy. Even though the illegal world of drugs and hitmen was dangerous John chose to raise both of his sons within the Devils. Grooming Dean from birth to one day run his empire. Teaching Sam, the younger son, to be loyal and follow the chain of command.

Dean was gifted anything and anyone he desired in life. He can admit that it made him a little spoiled, but more so that it made him impatient. It didn’t help him any that he was exceptionally attractive with his gorgeous green eyes, striking cheekbones, and pouty lips. He was a natural charmer that got him whoever he wanted. But he was more than just a spoiled little pretty boy. Dean Winchester could be evil. Standing a little over six feet he was a wall of rippling muscle. He was well versed in hand to hand combat and knew his way around a shooting range.

He was dangerous. Dean has killed too many men to keep track of, all in the name the Devils of course. When he was four-teen he started to enjoy the torture and killings and even began to look forward to his enemies grovelling and begging for their lives to be spared. He relished the day John decided Dean was ready handle “work” business by himself.

When Dean was twenty years old his father took ill, fearing the worst, he made Dean the new head of the Devils. John made a slow and agonizing recovery, but within three years he was back to full health. It was decided that Dean had done such exceptional work in his three years of leadership that we would continue his position as head of the gang. Dean would never admit it, but he was willing to kill to keep his position. He got off on the power from being the most feared man in the city. He'd never have another man tell him what to do again.


	2. A Typical Day

**Notes for the Chapter:**

> Still don't know how to format.

Dean Winchester was currently sitting in a business meeting, once a week he had his advisors gather at his main office to fill him in on every detail of the previous week. He liked to be in complete control, that included knowing all that was happening within his vast and illegal empire. Today he was particularly impatient. Sam, his brother, was droning on and on about the new office construction plans that he’d been working on. Dean looked at his watch for the third time in the last ten minutes.

“Sammy. Can we speed this up please? I’m falling asleep over here” Dean sighed with a fake snore causing a few chuckles around the table.

“Fine Dean. I’m done” Sam replied with an eye roll. With that the meeting was finished and everyone got up to go their separate ways. 

Truth is, Dean was just preoccupied. He was distracted thinking of the busty blonde that was tied up in his basement. He left her naked, blindfolded, and bleeding this morning. Every time his mind drifted to the way she cried and screamed as he sliced into her skin the previous night had him fighting of an uncomfortable erection. But now that the meeting was over he was free to go home and see if she had survived the day.

Dean left his office with an entourage of personal security behind him. As per usual they walked him to his chauffeured town car and then proceeded to follow him home in SUV. Dean didn’t like thinking that he had to be protected, like he was weak. But he enjoyed the rush of power he got from knowing so many people would risk their lives for him.

When Dean got home he wasted no time rushing from the car into his house and practically ran down to the the basement. His men called it his PlayRoom and he secretly loved it. He took a moment outside the door at the bottom of the stairs to gather himself and take a deep breathe, he didn't want to go inside too excited if she has bled out and died while he was at the office. Dean held his breathe and gave a knock to the door, he smiled a wicked grin and felt himself beginning to stiffen in his pants when he heard a scream and a cry for help. To his delight the busty blonde was still alive and as he expected she heard the knock and thought it was anyone but him. He sauntered into the room and almost moaned at the sight of her.


	3. Flashback to the Blonde

**Notes for the Chapter:**

> This is my first time writing smut, please don't be too harsh.

*FlashBack*

She was the young twenty-something daughter of a foolish man that owed more money than he could pay back, Dean didn't even bother to remember her name. She had big voluptuous breasts and was toned from many days spent at the gym. Ironically she had gone up to Dean in his club and chatted him up. She was clueless to the fact that dean would be taking her home regardless of her willingness. Dean found it amusing that she thought they were going back to his house for a one night stand.

“Your house is huge” the woman breathed trying to sound sexy “are you over compensating?” she added laughing at her own joke. 

“Shut the fuck up” Dean grunted as he gave her a rather hard push through his front door.

“Oh! I like it rough honey, lets say we take this to the bedroom?” with a wink she tried to grab Deans hand and drag him forward. He was getting annoyed of the awkward way she was attempting to sound sexy and instead of letting her touch his hand he pulled his away and walked around her.

“Come on” he deadpanned knowing she’d follow him regardless of the rude way he was treating her. They always did.

He lead her to the doorway at the top of the basement stairs. Allowing her to go first he took the opportunity to ogle her ass. Once through the second door Dean gave her a moment to take in the room while he locked the door behind them with the numbered keypad. It was a large dimly lit room with various tables and cages placed haphazardly throughout it. The left wall was covered in sex objects of all types. There were various sizes of everything and the bright colours always cause people to see that wall first. The right wall was his favourite. It was an arrangement of tools and torture devices. His favourite thing about that wall was seeing the reactions when it is finally noticed by his guests. 

Upon seeing her look to the right Dean pushed the young woman so hard from behind that she tripped in her ridiculous high heels and fell to her knees with an “Oomf”.

“Now” he announced with a clap of his hands. “You have five seconds to get naked before I cut that dress off of you” walking over to his right and plucking a short sharp knife off its spot on the wall. “And I don't promise to be gentle” Dean added with a grin turning back to his soon to be victim.

“W-What? I don’t know what you thin-“ she started to say but then stopped half way through as the gravity of the situation dawned on her.

“Thats five. I love doing things the hard way” he announced as he started to stalk back towards the attractive blonde still kneeling on the floor. She took in the distance between them and just as Dean hoped, she scrambled to her feet and stumbled back to the door they’d just entered. She pulled to no avail, she was locked in.

He strolled up behind the woman, forcibly spinning her around with a firm grip in her hair and toyed with the knife along her cheek. Rubbing his growing clothed erection against her Dean was enjoying the way she was trying to free herself from his harsh grip.

“You really should listen to me” Dean breathed into her face as he ran the knife down her neck.

“P-please stop dean, I’m not into this sort of stuff” she almost cried struggling in his grip, attempting to push away with all her strength.

“Oh baby! You gotta stop talking like that. You get me too excited and I won’t be able to cut you up before I fuck you” Hearing deans words and feeling his erection on her had the woman crying and screaming for help.

As turned on as he was, Dean was annoyed with the sound of her voice. He let go of her hair and slapped her hard in the face. Grabbing her by the hair again he pocketed the knife and dragged her over the the table in the middle of the room. He picked her up and threw her down on the middle of the table. Tying her hands with straps hooked to the sides, he made sure to make as much eye contact with her as he could. Intimidation is his specialty.

Reaching behind his back Dean pulled the knife from his pocket and placed the tip to the centre of her chest while he covered her mouth with his hand so she would hear his following words.

“I will only warn you once. You're voice is driving me insane. Stop talking or I will cut your tongue out. Please please don't stop crying though, it’s making me so hard” Dean finished talking with a moan as he finally removed his handed the knife. Taking in her tear stained face and trembling body he was getting increasingly turned on. 

He stood back from the table to remove his own clothing before stepping forward towards his victim. Picking up the knife again he began by cutting away the spaghetti straps covering her shoulders, making sure to knick her with the tip of the knife only when she started to struggle too much. Next Dean moved back down to her chest and pushed the blade in far enough for blood to begin to form around the tip. He dragged the knife down her chest tearing the dress and leaving behind a trail of blood and sliced skin behind, stopping at her bellybutton he used his hand to rip away the rest of the material. To his delight the woman was not wearing a bra or underwear. 

“Do you know why you're here?” Dean questioned running his hands over her body smearing the blood. Seeing her shake her head he rolled her eyes “you can talk to answer me”.

“N-n-no”

“You are here cause your daddy isn't very good with money. You're the only thing he had to offer me. So I guess that makes me your daddy now, huh?” chuckling at his own words and her renewed tears Dean started giving shallow cuts here and there along the woman's ribcage. “I’m going to play with you until I get bored and then I’m going to kill you” Dean blatantly stated.

Dean walked over to the left wall and grabbed a few things before returning to the woman who was now sobbing almost uncontrollably. He made a grand show of placing everything beside her. Two rather large matching black dildos, a set of steel nipple clamps, and a spreader bar for her legs. 

Placing the spreader bar on the willing woman was a challenge that Dean anticipated, but eventually he got her hooked in. Next Dean climbs on top of her on the table and began kneading her perky breast with his rough calloused hands. 

“I’m going to start cutting these until you calm yourself down. Hopefully by the time i’m done theres enough left to play with” he all but yelled over her crying. When Dean started slicing her breasts he was a deadly mix of vicious and meticulous. Soon she was covered in blood and her cries had all but subsided. Happy with the result of his handiwork he declared that she had calmed down enough and put down the knife for now.

The blood covered woman was now eyeing her tormentor as he picked up the set of nipple clamps and reached for her left nipple. Twisting and pulling it between his fingers he felt it harden under his touch. Maintaining eye contact with his victim, Dean situated himself so he was laying on top of the woman and attached his mouth the abused nipple. He sucked hard and fast like he was trying to milk her. As blood rushed to his cock he ground it against her leg licked at the blood seeping from the cuts he'd previously made, he eventually lifted his head and attached the first clamp. He used his right hand to apply the same treatment to the neglected right nipple. Once both were red, abused, and clamped he sat up.

“Now that is a beautiful sight"

Dean reached for the closest dildo and thrust it towards her mouth. “Open.” She reluctantly opened her mouth and he immediately began to face fuck her with the toy. Taking his cock in his hand he began to stroke himself to the rhythm of the toy. Pushing the fake cock as far as it would go Dean made her gag and choke as she was forced to deep throat and could no longer breathe. Her vision got cloudy but the dildo was taken out before she could black out.

“Make sure its nice and wet baby, daddy’s gonna put it in your pussy next” dean thrust the toy twice more before pulling it out and crawling back on the table to lift her legs trapped in the spreader bar.

He eyed her shaved pussy and almost second guessed his decision to fuck her with the toy. She was dry and he wanted to be the one to tear her insides. But he had planned this out already and didn’t feel like going off book. Dean lined the dildo up almost came on the spot as she screamed in agony when he forced the too large toy into her dry cunt. Thrusting it a few times he left it inside her and ran a thumb over her asshole.

“Because this whole mess is actually your fathers fault and not your own, I will give you a choice. I can fuck your ass with my cock right now or I can fuck it with the other dildo. What do you want?” Just as he anticipated, she chose his cock and he grinned devilishly as he slicked himself up with spit and bottomed out in her ass with one hard push.

She screamed and cried with a newfound energy he wasn't sure she could muster. Dean was quick to set a brutal unforgiving pace. The bleeding he caused only spurred him on. Picking up the knife again Dean renewed with previous slicing of the poor woman. Fifteen minutes of his brutal pace and painful cutting had Dean ready to blow.

“All that foreplay is going to make this a quickie baby, you're just too sexy screaming covered in blood” He thrusted inside her ass a few more times and then stilled as he came deep inside her abused hole. Removing his cock from her ass, he watched a small pool of blood and cum seep out and gather on the table. 

Dean stood and walked to a small sink in the corner of the room, he got a cloth and cleaned himself up. On his way back to the woman Dean grabbed a blindfold off the wall. He tied it around her eyes and picked up the black toy, unused but just begging for it. He wordlessly rolled the fake cock across her stomach coating it in blood. Trailing it down her body he realized he’d almost forgotten to carve his name into her. It was his trademark move after all. So, he drove the dildo into her unsuspecting bleeding asshole and held down the spreader bar as she flailed and jerked from the sudden agonizing intrusion. 

Dean picked up the forgotten knife and carved the large deep letters of his name into one perfect thigh at a time. Once he was satisfied with his work, Dean straightened up, gathered his clothes from the floor and left the room.

*End FlashBack*


	4. Morning After

**Notes for the Chapter:**

> Super short.

Entering the room Dean could see that the woman had indeed survived the night and half day she was left bleeding. She was surrounded by a large puddle of blood and urine. 

“Honey I’m home” he mocked the woman hoarse from screaming for help. “I’m so glad you're alive. I would have been pissed if I didn't get to ill you myself. It’s all I was thinking about today” he added just to torment her. 

The ringing of the phone in Deans pocket made him pause and huff in annoyance. Grabbing it out of his pants he could see that he had a text from Sam.  
SAM: Cops at the club.

Sam knew about Deans basement guest and would only have interrupted him if it was extremely important.

“Well baby, its your lucky day. I’ve got some business to handle” sliding the phone back in his pocket, Dean picked up the knife lying beside the woman and plunged into her gut and pulled up. He removed the blindfold to watch the life leave her eyes. It was his favourite part and he rarely missed an opportunity to see it.

Dean employed a whole team of people whose sole job was to clean and sanitize after him. He knew by the time he came back with a new victim that this room would be spotless and the body would be taken care of. He called them his personal crime scene cleanup crew, they went around the city cleaning up after the Devils.

Sam had sent a text to Dean about the police as a precaution, if they had a warrant to search the club then they likely had a similar warrant to search his house. They tried this everyone in a while, random searches over circumstantial evidence. It rarely yielded results. The Devils were too careful, Dean made sure of it.

DEAN: Let them take 5

Dean sent a quick text to Sam letting his know that if there was a warrant then they would have to risk five low level newbies to preoccupy the cops. He couldn't have his basement searched before the cleanup crew finished. It was something they often did, letting a few newbies be sent to jail in the name of the greater good. 

Making his way back upstairs Dean decided he would take a shower and get dressed while waiting to hear back from his brother. Walking down the hallway and into the large foyer that connected the front doorway to the living room, kitchen, and upstairs he could hear the cleaners pull up outside. Going up the main staircase Dean mentally chose what clothes he would change into after his shower, knowing full well if it wasn't a suit then he always wore plain jeans with a plain t-shirt, sometimes dressing it up with a plaid shirt layered overtop. While he scrubbed himself, Dean thought about the woman he'd just killed. It was typical. He was getting bored. Sure it was exciting during the torture, but he was finding it less and less satisfying afterwards. When Dean was finished washing he went hopped out of the shower and strolled into the connected bedroom. Walking into his larger than necessary closet he picked the first things he saw. 

Once dressed and ready to see what all the fuss was about, Dean fished his phone out of the pile of dirty clothes and called Sam.

“What happened?” Dean said without a formal greeting towards his brother.

“Nothing Dean, false alarm, didn’t you get my text?”

“No, I was in the shower”

“Oh, well I think they were just trying to intimidate us. They didn't have warrants, they didn't even come inside” There were noises of too loud music and people yelling in the background so Dean knew that Sam had stayed at the club to keep an eye on everything with the police. Knowing the club was in good hands, Dean said goodbye to his brother and hung up the phone.

“I need to to some pie” muttering to himself Dean went down to his kitchen and began the search for some pie.


	5. Lisa

Lisa Holland is different. She’s naive, oblivious, innocent, and all around pure. All of these harmless attributes are what make her stand out from the rest of the woman you'd typically find in LA. But above all else she is normal. Lisa is a cashier at a local homegrown bakery. She has worked there since she was fifteen, now six years later she is twenty and practically family to the little Italian couple that own the shop. Lisa is an average looking young woman being only 5’5 with long ginger hair, large green eyes, and simple curves. She was attractive enough to have the attention of men, but was far too unaware of their advances to notice an flirtations.

Today was an unusual day for her, the power had flickered in the middle of the night and her alarm clock had reset. For the first time in six years, she was going to be late for work.

The birds chirping outside her window was what woke her. Lying in her small one bedroom apartment Lisa knew that something was wrong, she always woke up before the birds. She shot up with a start to check her clock. 

“No no no” panicked she reached for her old school flip phone and pressed the side button to show the time. “What?” still talking to herself, Lisa jumped out of bed and raced around her room grabbing clothes, keys, shoes, and her purse. She quickly brushed her hair, and threw on her clothes. Running out door in her pink sundress and white flats she almost forgot to lock the doors.

Work wasn't a long walk away, usually Lisa gave herself a half an hour to take her time and get to work a little early. Today though, she was forced to jog the ten blocks.

“I can’t believe this” Lisa quietly berated herself when she stopped at a crosswalk waiting for the light to change. 

“Oh my God! Darling I thought you died!” Mrs. Grimaldi, the small but loud Italian woman yelled as Lisa walked in the front door. In reality she had not looked at the clock, nor had she noticed that Lisa was even late. But upon hearing the front door open she realized that her favourite employee was in-fact half an hour late.

“I’m so sorry Mrs. Grimaldi! My alarm didn't go off last night, I think the power went out at my place overnight” Lisa rushed he apologize and explain while she went around the counter and picked up her name tag.

“Darling Darling, I’m just being funny” the old woman laughed to herself. “You’re fine. Six years and you’ve never been late before”.

“No no, I’ll stay later. I feel so terrible” now mumbling to herself because the old woman had wondered into the back to check on the baking.

True to her word, even though she was told to go home, Lisa stayed and hour after her shift to make up for being late. She had cleaned everything in sight and was now convinced she could go home and not feel guilty. She yelled her goodbyes to the Grimaldi’s out back and left through the front door of the bakery. Leaving work she turned right and started the ten block trek home.

Lisa was so deep in thought, imagining the best way to ensure she would never be late again, that she neglected to see the light above her change as she stepped off the sidewalk. She got half way across the road when a shiny town car slammed on its breaks, narrowly missing her. The driver blew the car horn and rolled down its window to yell at her. Lisa jumped back in fright and looked up startled. She watched like a deer in headlights as the back door of the car opened and a very attractive man in jeans and a red plaid shirt stepped out.


	6. First Meeting

“Hey-” the attractive man began to yell as he climbed out of his car. He assumed the woman would see his face and know who he was. But there was no recognition. The stranger didn't know that she almost got hit by Dean Winchester. When he saw her face his mind went blank, his previous sentence forgotten. This poor stranger that almost got run over by his car, was absolutely beautiful. She looked so scared standing in the middle of the road in her little pink dress. To his dismay the cars behind them started to honk their horns and the girl seemed to snap out of her shock.

“Sorry!” the scared young woman shouted back sheepishly before running across the road to the safety of the sidewalk. Dean had to find out who she was.

Lisa was so embarrassed, she’d been daydreaming and had almost gotten hit by a car. She made sure to pay extra attention at every crosswalk and arrived home safe and sound. Paying such close attention to the sidewalk and the lights caused her to miss the fact that she was now being followed. The car that had almost run her over made a hasty last minute turn and was now trailing behind her.

Arriving at her apartment Lisa replayed the weird day she’s just had. The worst part being that she had forgotten to stop on the way home to pick up groceries, now she had nothing to eat for supper. 

Even though it was mid June and scorching during the day, it was chilly enough in the evenings to want to change out of a small sun dress. After a quick shower and a change of clothes Lisa had a light snack of an apple she found in the bottom of the fridge. Now that she was dressed for the weather, in jeans and a sweater, she grabbed her purse and left for the grocery store.

Dean knew as soon as he saw the woman in the street that he had to know who she was. When he jumped back in his car he instructed his driver to follow the woman. They followed her for a few blocks before she finally stopped and entered an apartment building. Hoping that she didn't live in this shitty looking building he pulled out his phone and texted off the address to Paul, a lackey of his.

DEAN: 224 Kingston place. Redhead.

Knowing that Paul would know the text was to find out who he was looking for, Dean put his phone down and relaxed in his seat expecting a long wait.

Fifteen minutes later Dean received an e-mail from Paul, apparently there were two redheads in the building. Quickly dismissing the first one from her picture, he was left with the one he was after. Dean now knew everything about her.

“Lisa Grace Holland” Dean mouthed almost silently.

About half an hour later Dean watched Lisa leave the building. She looked more prefect than he remembered. He directed his driver to tail her again. Deans anticipation grew as his imagination ran wild. He couldn’t wait to have her. Unfortunately her short walk ended at the grocery mart a few blocks away, Dean was a little disappointed.

Dean got out of his car and followed the beautiful woman into the store. She picked up a basket so he do too. She walked up and down every isle so he did too. Finally he had enough watching, he had to talk to her.

“Excuse me?” Dean said to the woman he had been following.

“Oh, sorry” She quietly apologized, sliding over assuming she had been asked to move out of the way.

“No, actually I should be apologizing to you” reaching out to gently turn Lisa by the shoulder, “I think I almost hit you with my car earlier”. Trying his best to look a believable mix of guilty and embarrassed, Dean savoured the feeling of his large hand on her body. 

“What? Oh my Goodness, no no. That was my fault earlier, I’m so sorry” Lisa rushed to apologize for earlier upon realizing that she recognized the man from the car.

“I’m Dean by the way.” Finally taking his hand off of her shoulder and thrusting it in-front of her for a formal introduction, completely ignoring her apology.

“Lisa” She replied with a polite small and met his hand for a quick shake. “Funny how we ran into each other here”

“Yeah, funny. Let me take you out for supper. To say sorry.”

“You really don't ha-“ Dean cut Lisa’s rejection off, not ready to take no for an answer.

“Come on. I know the perfect place.” Grabbing the half full basket from her with one hand and guiding her by the waist with the other, Dean steered her towards the exit.

Not seeing any harm in the offer, Lisa let herself to be led out of the store and over to Deans car. Now that she was able to observe the vehicle without the fear of getting run over, Lisa saw that it was shiny, and looked brand new. Albeit, she kew nothing about cars, she could tell it was expensive.

“I like your car … it’s very fancy”

Flashing an award winning smile, Dean was pleased by the innocence of her compliment. Opening the car door like a gentleman, he was able to steal a great view of her ass as she slid into the seat. Closing the door behind her and walking to the opposite side of the vehicle Dean took a moment to hide his excitement.

Deans breath hitched when got in the car and saw the sight of her. She looked so tiny and helpless just sitting there expectantly waiting for him. He knew in that moment he would have her.

“So tell me, Lisa, do you live around here?” They dove into small talk for the twenty-five minute drive.


	7. Bad Date

**Notes for the Chapter:**

> Working on smut for the next chapter.

That was the best twenty-five minutes of Deans life. He started the drive by asking questions he knew the answers to, just to see if she would tell him the truth. Paul’s detective work was spot on, everything was correct. Once his inquisition was over it was her turn to ask questions. All of Deans answers were ambiguous and half truths.

The restaurant they arrived at was a place Dean frequented quite often, it was owned by the Devils. He was recognized right away and was treated accordingly. They were rushed to his usual table on the upper level by an attractive brunette. Lisa was too busy marvelling at the elaborate interior to notice how everyone seemed to recognize the handsome man escorting her.

The restaurant was one of the oldest buildings in LA. It was bought by John Winchester in the late 1990’s and was remodelled by Dean a few years ago, though he kept the original name "Hell Hole", he took full ownership from his father. He hired a decorator who overcharged him an arm and a leg. “Modern yet Classic” was the way she kept calling it. To Dean it was just an old brick building with a black and white inside, but sam loved it, so Dean overpaid and kept it.

“Wow, this place is really nice… maybe we should go somewhere else though, it looks expensive” She murmured awestruck.

“Don’t worry about it darling” 

Marching up the stairs Dean had a great view of the two woman he was following. He couldn't help but notice how small Lisa was. She had curves, but they weren't as noticeable. There was just something about her though, just watching her walk up the stairs was making him hard. Willing away an unwanted boner for the second time that day, Dean had to look away from his date.

The table was a booth situated in the back corner of the second floor. It was easily big enough to fit the usual escort of security that accompanied him. Watching Lisa slid into the booth made Dean thankful he had left his detail at home, he was already too addicted to being the sole object of Lisa’s attention.

“We’ll take a bottle of wine.” Dean ordered from the attractive brunette waitress without looking in her direction.

“Oh…. um… I don’t drink actually” Lisa tried to say in the nicest way possible.

Dean was surprised. He hasn't met many people who turn down free wine at a nice restaurant from an attractive man.

“I don’t think i’m dressed up enough to be here” Suddenly self conscience of her casual clothes, Lisa was worried they would be asked to leave.

“You look great” Dean couldn’t help but grin at the innocence of her comment but stopped abruptly at the stiffed laugh of the waitress. Dean was mortified.

Hearing the laugh, Lisa’s cheeks burned red in embarrassment. Dean wanted see other parts of her turn red, but at his hand and not from the shame of being judged by this painted up whore. He is going to kill her.

“Thank you so much Dean, but I don’t think I should be here.” Lisa was apologizing while crawling out of the massive booth. 

Lisa was faster than Dean thought she would be. By the time he had slid out to stop her she was already walking away from the table.

“Wait, Lisa. Stop. Please sit back down.” For the second time, Dean was surprised by his new friend. She pulled her arm away and continued to apologize and walk away.

Dean was seething in anger. He pulled himself together long enough to call his driver and tell him to take Lisa home, only to be told she had taken a taxi before he had called. Dean was now in a blind rage.


	8. Punishment

'I’m going to kill that stupid cunt. She thinks because I screwed her once way back in the day that I have feelings for her? She is about to have a rude awakening.' Deans mind was running rampant.

Marching up to the woman Dean wordlessly slapped her in the face, grabbed her by the throat, and dragged her down the stairs and out of the Hell Hole. Once outside he pressed her into the side of his waiting car.

“You’ve made a huge mistake.” He finally broke the silence before slamming her face into the car door she was forced up against.

Pushing her into the backseat Dean instructed his driver to take them home. Having twenty minutes to calm himself was good for Dean. It allowed him to plan out exactly what he was going to do.

'Well I am horny, maybe this is a good thing. I have that wooden horse I’ve been meaning to try. Thinking the whole way home, he came up with a rough plan.' He wanted to prolong this one.

“Take her downstairs.” Ordering his men, he strut passed them and went into the kitchen for a quick supper.

The men rushed to follow Deans orders. Heaving the woman, a few recognized from the restaurant uptown, down to the playroom. Word had travelled fast through the Devils. The scene in the Hell Hole had been viewed by many and was spread around by the time Dean arrived back home. Everyone knew the very likely fate of the poor attractive brunette waitress.

As Dean expected, the woman had been stripped and placed in a cage on the floor of the playroom. She had not woken by the time he finished supper and went down stairs.

“Rise and shine, sweetheart!” Dean stomped around the room loudly, retrieving a bucket of cold water from the sink the back of the room. 

“I said wake the fuck up!” Starting to get annoyed now, Dean threw the cold water on the passed out woman in the cage.

Groaning from the headache and sputtering from the water, the poor woman was slowly realizing where she was. Naked, wet, and afraid, she eyed Dean standing in front of her with an empty bucket.

“Dean? … What the fuck. Let me out of here.” Not yet noticing the room she was in, she shouted and swore at Dean shaking and banging on the cage bars.

“You were very rude today. You ruined a pretty important dinner. So now, I am going to ruin you.” Smirking, Dean undressed himself.

“What? Dinner?” Memory slowly coming back. “You mean with that skank in the Hell Hole?” Having no idea she was making it worse, she continued. “Why do you care about her? We had more fun then she’d ever give you.”

“Stop. Talking.” All the time Dean had taken to calm down was for nothing. This woman was getting under his skin again. “We are about to have some fun alright.”

Now the woman was really seeing where she was. The dim lite room. The dark red walls covered in tools and sex toys. The various cages and tables. The stale smell of disinfectant. She was frightened beyond belief. 

“Dean… I’m serious. Let me out!” 

“I just have a few things to get ready first, sweetheart” Dean mocked.

Slowly striding around the room he collected the items he would need for the evening. The wooden horse he had not gotten the chance to try out yet, and rope to tie her to it. Clamps for her nipples with weights on the end of long silver chains that will hang just above the floor. A bamboo cane for her punishment. And lastly, the key for the cage.

“Alright, now its time for some fun.” 

Unlocking the cage door for the crying woman, Dean was disappointed when she backed herself up instead of making a dash for freedom. 

“Please… don’t.”

“Out you go.” Dean reached in to grab her by the hair and drag her out by force. He was pleasantly greeted by a punch to the stomach. He loved when they fought back. Of course she had no real hope of fighting him off, it still got his blood rushing.

A slap to the face made her still for long enough to grab her arms. With the rope in one hand Dean managed to get both her arms behind her and tie them there. He wanted to prolong the struggle, but her crying was annoying him too much at the moment.

With her hands tied, she was forced onto the wooden horse he had drug into the centre of the room. The woman was just tall enough to touch the floor on her tippy-toes. The wood still rubbed her pussy uncomfortably. She wiggled around trying to get off, moaning when the sharp wood dug into her clit.

“I love those sounds baby.” Securing her with the rope, Dean made sure to moan along with her. Reaching a hand out for her nipples, he began to pinch and pull at them. Forcing them to harden under his brutal touch. Considering piercing them, he decided to clamp them for now.

Attaching weighted nipple clamps to his victims was one of his favourite things to do. He loved seeing the nipples get red and swollen under the abuse, and then to hear the moans and sounds they always made when he put on the clamps. 

“Now, I’m going to spank you with this until you bleed or pass out.” Waving the cane in front of her face.

Dean started on her ass nice and slow, giving her time to expect each blow. Slowly he mixed it up so she didn’t know when it would come next. After a few minutes she was crying and begging for him to stop. Deans mind wondered back to Lisa, and his interrupted dinner. He allowed all of his pent up anger out in the punishment, her ass would be bruised and bleeding by the time he was done.

“You. Really. Fucked. Up.” Accentuating each word with a whack of the cane on her already bruised backside.

Five more minutes of the cane and she couldn’t talk anymore, she had been beaten into a sobbing bloody mess.  
Getting horny at the sight of her, Dean was as hard as a rock. Giving his cock a few slow strokes, Deans mind wandered back to Lisa again. She would be so pretty crying for me. 

“You want my cock, sweetheart?” Dean teased the woman.

“P-p-pl-ple-please. S-s-st-stop.” The words making Dean moan out loud.

Dean walked over to the far right wall and grabbed a small pocket knife from its hanging place. He intended to cut the woman down and fuck her on the cold tiled floor. But when he returned to her side she was still squirming and groaning in pain and he couldn't help himself, he had to make her bleed a little more.

He cut the rope holing her in place on the horse so he could slide her back and forth. Straddling the horse in front of her, Dean forced the woman to grind her pussy and clit on the rough wooden board. With a tight grip on her waist with one hand, Dean knocked her cheek with the pocket knife overtime she came close to him. 

When the woman pussy was sufficiently red and abused it was time for her to get fucked. Dean pulled her off with a hand in her hair and threw her onto the floor on her stomach.

“I’m gonna fuck you now, do you want that baby? You want my big cock in your tight hole?” Dean continued to tease the woman, completely ignoring her pleas for him to stop.

Realizing she had not once apologized for earlier, Dean decided to give her a chance to do so now.

“If you apologize to me, I won’t kill you after I fuck you.” He baited the sobbing woman.

“I’m so-s-so sorry. Please, I-I promise, I’ll never do it again.” Not sure what she was being punished for anymore, the woman rushed to get any words out before Dean changed his mind.

“Thats a good girl.” Petting the back of her head, Dean lined his hard shaft up at the entrance of her dry abused pussy.

Thrusting in quick, Dean set a brutal pace. With no time to adjust to the feeling, the woman screamed out in pain, begging for him to stop.

“Oh yeah! Just like that, baby!” 

The immense pain of her ass was worsening with every smack of his body against her. Looking down Dean could see the blood dripping down and covering his cock slamming in and out of her pussy. It was intoxicating.

Ten minutes in, they were both a sweaty out of breath mess. Their bodies were slick and sliding against each other. The floor beneath them now covered in a sheet of blood, sweat, and tears.

“I’m not going to last much longer.” Dean talked to himself, knowing the woman wasn’t listening.

Stopping fucking her to flip her over onto her back, Dean made sure to move the hair off her face so she could see him. He was going to kill her, and wanted to make sure she could see it coming.

“Look at me.” Dean smacked he face a few times to get her attention. “Thats it. Right here, sweetheart.” 

Plunging back into the crying woman, Dean picked up the knife lying to his right and brought it up between them. Upon seeing it, the woman screamed and cried hysterically. It was exactly what Dean was hoping for.

Dean carved his name into the woman’s chest, it was rough and almost unreadable. She kept squirming around still impaled on his member, annoying him when the letters turned out all cock-eyed.

“You fucking bitch. You messed up my favourite part!” 

“Please, stop! You promised!”

“I know sweetheart, I lied. I fucked you, and now I’m going to kill you and then come inside your dead body. You're going to be buried in my backyard by the morning.” Dean taunted the woman for his own enjoyment. 

Finally Dean had enough. He slammed the pocket knife down into her heart. She sputtered and gasped as her mouth filled with blood. Dean watched the life leave her eyes as he continued fucking her. When she stopped moving he finally allowed himself to come, deep inside her.

Dean knew that this dead woman wouldn’t be buried in his backyard. He was just liked to get under their skin before the kill. He was in the moment and couldn’t think of anything else.

Standing up and strolling to the sink in the back of the large room, Dean quickly wiped himself down. Once he had retrieved his pile of discarded clothes from the floor, he went upstairs to make a phone call about his little Lisa.


	9. Back to Work

**Summary for the Chapter:**

> Smallest chapter ever.

Lisa was so embarrassed. She knew as soon as she walked into the Hell Hole with Dean, she didn’t fit in there. She didn’t look like the other women parading around the restaurant. 

After her ashamedly rude exit on her date, Lisa ran downstairs to the front door. Catching the first taxi in sight, she now had thirty minutes to replay the evening in her mind. The more Lisa thought, the more she was embarrassed of her actions to her poor date. She could get over her ugly clothes and being laughed at by the waitress, but she could not forgive herself for the way she ran away from the nice man that was just trying to apologize. 

“Thanks.” Lisa thanked the man when he pulled up to her building. Handing over the most cash she had ever spent on a cab in her life, she realized that she had just spent all of her grocery money on a taxi, and now had nothing to eat for supper.

Tired, humiliated, and hungry. Lisa trudged up the stairs of her building hoping to just crawl into bed. She barely made it under the covers before she was asleep.

Her dreams that night were filled with Dean in his plaid shirt and fancy car. She dreamt he was driving her around the city, the wind blowing her hair through the open window. Music blasting loudly from the speakers and a beautiful toothy grin plastered on his face the whole time.

The next morning Lisa had woken up well before her alarm went off. She was still so shook from being late for work yesterday that she had slept lightly and woke up with the rising sun. Checking her alarm clock she saw it was only six o’clock She had Forty-five minutes before her alarm went off. Trying to go back to sleep was useless, she was up for the day.

“Ugh, I should get up I guess.” Mumbling to herself, she slowly sat up, stretched, and yawned.

Having plenty of tome today, Lisa took her time to shower and get ready. Washing her hair she let her mind drift back to the previous nights dreams. Dean really is attractive, I can’t believe I ran away from him yesterday. I was so rude. Her mind was full of the handsome mans face.

Once showered, hair dried, and dressed in a short pink pleated skirt with a white long sleeve button up blouse she went in search of her shoes. The nude pumps she was looking for were found in the bedroom closet.

She then dug around in the fridge for something to make for breakfast. Finally coming across the instant oatmeal and box of raisins in the cupboard Lisa had found her meal. Taking five minutes to make it and five to eat it, it was time to leave for work. She wouldn’t be late today.

It was a beautiful day outside. The sun was shinning and there wasn't a cloud in the sky. Lisa took her time to enjoy her walk to work. She loved this city, it was always bright and full of life. Putting in her headphones to tune out and ignore the cat calls she got every morning on her way to work, she missed the fact that she was being followed. 

“On time today, I see.” Mr. Grimaldi greeted Lisa with a chuckle.

“Oh yes, I will never be late again, I promise!” She retorted back. “How’s your morning so far?” 

“Same as always Darling.” With that, they both set off into their daily ritual of setting up the bakery for the breakfast crowd.

That was the busiest day the little Italian bakery nestled in a forgotten corner of east LA had ever seen. It was a beautiful summer day and it seemed like everyone was out taking advantage of the weather. It was so busy that Lisa’s unknown follower had been able to sit in the bakery all morning without drawing attention to himself.


	10. Business Meetings

Dean had to made a phone call to his brother before he went to bed. He needed to know what Lisa did when he wasn’t around. 

“Sammy. I need a guy.” Dean was not known for polite greetings.

“Wow Dean, I thought you could find your own dates?” Chuckling at his own joke, Sam knew Dean wouldn’t laugh along.

“I met a girl. I’ll tell you about her tomorrow. I need someone to tail her in the morning.” He deadpanned, all serious.

“Fine. Fine. I’ll send Mikey over in the morning.” They said their usual goodnights and goodbyes, and hung up.

Dean was tossing and turning all night. What if she has a boyfriend and lied to me. I’ll have to kill him. And then I’ll have to punish her. She won’t like me very much after that. Dean couldn’t get his mind to calm down. He eventually fell into a restless sleep.

The boy Sam sent him the next morning was so new that Dean was sure he had never seen him before. He hoped he could be trusted with this task.

“Hey. You. Sam tell you what I want?” Dean questioned without any form of greeting when he walked down stairs he next morning and saw the boy standing there waiting.

“Yes Sir.” The boy all but whispered. He won’t last long. Dean thought to himself.

“Good. I have meetings all day. I want to hear about everything she does and everyone she talks to. No detain is too small, you understand me?” Dean was letting his boss voice come out. 

The boy didn’t have much to report back throughout the day. He sent a few candid pics every once in a while. She showed the same polite friendliness to everyone that came in, more-so the odd time someone came in with a small child. She was all courteous smiles and subtle rejection to the men that showed any interest. Dean was especially happy to hear that.

Dean had a lot of work to do today. There were a few business meetings, some products to review, and a couple people to visit. In other words; he had to find out know needed to die, go get the weapons to use, and then track them down and do it.

His day went by painstakingly slow. Dean just wanted to go see his new redheaded friend. He was already obsessed. It was only get worse from here.

Deans list of "business meetings" was short today, he only had three. Usually such a small number would disappoint him, but right now he was thankful. He wasn't going to ruin his name by rushing, no Dean would take his time and exert as much pain as possible. 

He took his chauffeured town car to a warehouse just outside the city. Pulling up Dean saw the usual three vehicles; Sam’s car, the cleaning crew vans, and the SUV that would have carried his victims to their fate. 

“Sammy, hows it going?” Deans nonchalant greeting to his brother would have been unsettling to anyone that could see the inside of that warehouse. 

A line of three chairs was in the centre. Each supporting a different sized man covered in varying mix of sweat, mud, and topped with a burlap bag over his head. A few feet behind the men there was a table set up with all of the tools he would need for the day.

“Oh I’m just peachy. I’d be better if tubby over there hadn't pissed himself in my SUV.” Sam sent the short fat man in the middle of the line of chairs an evil look.

“Don’t worry brother, I’ll make him pay for it.” Smacking sam on the back in mock comfort, Dean made his way over to the first man.

“Now, Mr. Hillel. If you can tell me why you’re here I will happily let you go. How does that sound?” Dean walked up to the man and bent down so he was at the same level, removing the mans hood he looked him straight in the eye and waited for his response.

“Dean. What kind of game are you playing? We both know why I’m here. You wanted more money than I’m willing to pay.”

“Oh no! Sorry, thats incorrect. You were so close. You’re here because I want to cut you up into little pieces and toss you into the ocean.” Dean taunted the poor man.

“I’m not afraid of you, Winchester.” The mans wavering voice betraying him.

“You will be.” Dean deadpanned.

Instructing Sam to move the other men out of his way, Dean walked around them to take a look at his tools. He considered just shooting them all right now so he could go find Lisa, but he thought better of it. There was a certain pride in being the most feared man in LA, he couldn’t compromise that.

“Lets get started.”


	11. Messy Work

Dean spent the better part of the next three hours cutting and tormenting the poor men. These three men had the nerve to cross Dean Winchester, they knew what they were doing and they knew the consequences. Each one was there for relatively the same reason. Taking something from the Devils or not giving something to them. They were beyond negotiations. There would be three people leaving the warehouse in body bags, one way or the other.

It was an art. The things Dean could do. It took skill, patience, and many hours of practice to get as good as he was. He knew just how to draw out the pain and suffering, only letting the victims die when he was finished having fun with them.

“You know, this ones kind of cute. Maybe I shouldn’t let him bleed out quite yet.” Looking at Sam for a reaction while ignoring the man bleeding out in front of him.

“I thought you had a new friend for that?” Sam played along with his brother. He’d heard this one a thousand times. Dean liked to get inside peoples heads, though he rarely followed through in situations like this.

“Oh I don’t know, Sammy, he’s got such a pretty mouth. My cock would look perfect right here.” Finally looking down at the now crying man, Dean tugged on the mans lower lip with a wink. “What do you think? Wanna taste?”

The last victim left was crying and shaking his head, not sure if the psychotic man standing in front of him with a knife covered in his blood would actually rape him before killing him. Why wouldn’t he. The things he just witnessed Dean do to the two men before him. He couldn’t take the chance.

“Just kill me, Winchester. Please. Get it over with.” Cried the man slowly bleeding to death on the middle of the warehouse.

“That hurts my feelings. Fine, no point in keeping you around then.” Before he could get a response Dean thrust the blade of the knife into the mans bleeding chest. Looking deep into his eyes as he twisted the handle, Dean felt blood rush down to his now growing cock.

“Damn, maybe I really should have used his mouth.” Dean mumbled to himself.

“Alright, record time.” Sam clapped his hands together and begin walking around barking out orders to get everything cleaned up.

Meanwhile Dean was stripping off his bloodied clothes and re-dressing into a new set. He always brought a change of outfit or two to every business meeting. Today was decided to dress up into a fitted designer suit. He wanted to show off to Lisa when he went to see her later. 

Thinking about Lisa made him realize that it had been a while since he had received a report about her. That made him tense and suddenly in a rush to go see her for himself.

“See ya later, Sammy.” Deans job was done. He did the messy work and could leave knowing that Sam and the cleaning crew would take care of the rest; they always did.

Waving a vague goodbye, Dean left the warehouse and made his way to the chauffeured car waiting for him.

“The Bakery.” Dean instructed the driver and sat back to enjoy the duel rush of the high he got from killing, and the excitement he felt from finally going to see Lisa.


	12. Bakery

The drive to the bakery was agonizing. Traffic had never seemed so bad before. Deans patience was running thin by the time they eventually pulled up. Realistically, the traffic was normal, maybe even a little lighter than usual. But Dean was convinced it was especially bad today.

“Fucking finally!” Pulling up to the little Italian shop, Dean hopped out of his car without a word to the driver and jogged up to the front door.

There was a small gold bell above the front entry way to the bakery that gave out a small angelic chime any time someone opened the door. It was the most perfect sound Dean had ever heard, and the smile Lisa flashed in his direction from behind the counter when she heard a presumed customer enter made his heart skip a beat.

She really was beautiful. It was the simple innocence of everything about her that made Dean want to claim her as his own. 

“Hello.” Lisa gave her usual courteous greeting in Deans direction when she heard the door chime. When she realized who had just come in, her cheeks burned red with the embarrassment of the way se acted the previous night and she slightly hung her head.

“Hi, Darling.” The sheepish way she was acting didn’t go unnoticed to Dean, and he was enjoying every second of it. “I’m glad you're working today, I wanted to make sure you were alright. After the way you ran off last night … Well I wasn't sure what to think.” He chose to play into her guilt, this was one of his favourite games. He knew he’d be able to get what he wanted if he kept her feeling bad.

“Oh Dean, I’m so sorry about last night, I’m terribly embarrassed. I don’t know what I was thinking, and after you went through all the trouble of getting us a reservation at that fancy restaurant at the last minute.” She was unknowingly playing right into his trap.

“Was it something I did? I’m sorry if I upset you somehow.” Dean faked his worry and distress, knowing he had her right where he wanted her.

“No! Oh my goodness, Dean. You were a perfect gentleman, really, I swear. I was jus-“ 

“How about a re-do? I mean a proper date this time.” Dean interrupted Lisa before she had to say out loud why she ran away the previous night. “I mean you kind of owe me.” Dean added with a cheeky grin when he could clearly see the apprehension on her face.

“I don’t know Dean …” 

“Your shift is almost over, I’ll drive you home and we can go from there. Give you no time to change your mind.” Dean stated before he could be rejected. Even though he was joking with he, he was also being selfish. He wanted her all to himself and he more than anything wanted to see her apartment.

When Paul had sent Dean everything there was to know about Lisa, he also sent him a few general apartment layout pictures from the rental ads online for the apartment for rent below Lisa’s. They looked terrible. The apartment was cheap, and it looked even cheaper. If it was as bad as he suspected, then he would be making some changes to her living arrangements tomorrow. 

“Ok, ok. Fine, I would love to.” Always polite, Dean Loved it.

“Perfect.” Dean flashed his pearly whites and went to have a seat to wait out the rest of Lisa’s shift.


	13. Her Apartment

Twenty-three minutes after Dean walked into the small bakery and convinced the new object of his affection to give him another chance, it was finally time to get her all to himself and drive her home.

“Alright Dean, lets get out of here.”

“After you.” Standing up and motioning for Lisa to go first Dean took a moment to admire her body again. He was making a habit of that.

Instructing Deans driver where she lived, even though they both already knew, Lisa sat back in the seat of the fancy car owned by the man in the fancy clothes seated beside her.

“Thanks for waiting Dean, I know you must have been bored.” Lisa was more glad that he waited to drive her home than she was letting on. Her feet where killing her, it was too busy of a day for her to be running around in the heels that she chose to wear.

“Nah, I liked watching you, Darling.” Dean winked at her, getting turned on when her cheeks flushed red and she quickly turned to face the window to try and hide it. 

When they pulled up the small apartment building, Dean was quick to jump out and run around to hold the door open for Lisa. He allowed her to go ahead of him and he followed close on her heels so she would have no doubts that he expected to follow her upstairs.

Dean had a mental checklist in his head of everything wrong with the building. The first thing was how lousy it looked from the outside. The next and probably most important was the lack of security to get into the foyer, if it could be called that. There was no lock on the front door, anyone off the street could follow her in at anytime.

“You can wait right here if you want, I live up on the third floor, its quite a walk up the stairs.” Drawing Deans attention away from the unlock able front door, he realized that Lisa was standing at the base of a staircase and was talking to him.

“I love exercise.” Dean joked, and started up the staircase to end any sort of rebuttal she might have. After seeing the state of the building so far he had to see what her apartment looked like.

They didn’t make conversation as they made the trek upstairs, Dean could clearly see that Lisa’s feet were bothering her. He was pleased that she had enough sense to not take her shoes off and walk up the decrepit staircase in bare feet. But the fact that she had to walk this far everyday had him enraged anyways.

“This is it.” Lisa mumbled quietly when they arrived at her front door.

Just as Lisa put her key in the key hole there was a loud ruckus from somewhere down the hall. Knowing exactly what it was, Lisa gasped and quickly opened the door. Pulling Dean through, she slammed the door behind them and turned the lock just as there was a bang on her door and a few yells on the other side.

“I’m sorry about that.” Lisa was a little scared, but she was used to it. Her neighbours got drunk a few times a week and would yell and make passes at her when she would walk past on her way home from work. “The people down the hall are a little loud.”

The banging on the door continued loudly. Dean could hear the neighbours drunkenly yelling out her name along with a few catcalls and profanities.

He’ll kill them.

“What the hell are they doing out there?” Dean questioned out loud as he reached for the door intending to confront the people on the other side.

“No! Don’t go out there. Sometimes they get a little rough. They’ll go away eventually .. just don't open the door, please.” Dean’s blood was boiling at the sound of fear in her voice. 

He will definitely kill them.

“They get rough with you?” He questioned, trying to calm himself down With deep breaths between each word. 'Calm down Dean.' He thought to himself. 'You don’t want to scare her yet.'

“Please Dean, just have a seat. I’ll get changed and they should be gone by then.” Lisa stood by the door until Dean turned to walk into the small living room, just incase he tried to open the door again. Not knowing that Dean was seconds from picking her up and moving her out of the way.

“Ok, fine.” Dean mouthed tightlipped. 'I’ll see them later anyways.' Dean was already making plans for them in his head.

Now that Dean had turned around he could finally see the inside of the apartment. It was atrocious. But somehow seeing her things everywhere made it seem less bad. He could tell that she had tried her best to make the small ugly space bright and feel like home, it was almost cute for what it was.

The first thing Dean saw was the lack of space it was an open concept living room and kitchen area, not even enough room for a table. Her living room was covered in pictures of family and friends. There was a small TV against one wall and a love seat barely big enough for two people across from it. 

“Make yourself at home, I’ll be right back.” With a final look back at the front door Lisa turned and went to her bedroom.

“Take your time!” Dean yelled back, not paying her much attention as he pulled out his phone to make a call. He instructed the man on the other line to come collect the rowdy neighbours. He wanted to deal with them personally.

With the bedroom door closed Lisa was able to drown out the sound of the banging on the door and really think about what she was doing. She had brought a strange man into her apartment, she’d never done something like that before. But she really liked Dean and she definitely owed him a second chance.

“Where are we going to go tonight?” Lisa yelled out the bedroom door. Realizing that she hadn't done laundry in a few days she was now limited to the clothes she could wear and had to dig something out of the back of her closet. She grabbed a floor length tight white spaghetti strap dress that showed off, in her opinion, too much cleavage.

“I know a place with the best food in town” Dean answered back with a grin.

When Dean’s men arrived a few minutes later the banging on the door stopped and he was able to relax. He was sitting on the couch and he spotted a picture on the table of Lisa and two older people, presumably her parents. 'She will never have to come back here.' Dean was admiring her smiling face in the photograph when the woman finally emerged from her bedroom.

“Wow, you look great!” Dean was stunned by the sign of her. He suspected there was a hot body buried somewhere underneath the baggy layers he had only seen her in, but this was batter than he could have hoped for.

“I forgot to do laundry yesterday, this is the only thing I could find” Lisa was blushing again.

“Gorgeous, darling.” It was slowly becoming Deans new life goal to make Lisa blush as much as he could.

“Um, I think they left, if you want to head out now?” Lisa was unaware of the fate that faced the poor fools that dared to anger her dinner date.

Dean used a guiding hand on the small of Lisa’s back as a poor excuse to finally touch her and he led her out of the apartment and then the building.


	14. Second First Date

It was a long and quiet drive, but it was a peaceful sort of quiet. Dean was enjoying the small space he had Lisa trapped in. She smelled amazing, like a bouquet of flowers, and he was able to just sit and admire her face for the first time since he met her less than seventy-two hours ago. She was beautiful. Time seemed to pass by slowly in the back seat of the car.

Lisa on the other hand, was not paying any attention to her date. She was too busy daydreaming while gazing at the passing city outside of her window. The fact that she was being stared at by Dean had completely gone unnoticed by her.

They had been in the car for a short while before Lisa realized that they were not going back to the same restaurant as the previous night. She had never been this far from her home before. She had a small moment of panic, maybe it was a bad idea to get into the car of an almost complete stranger. She hadn’t even told anyone of where she was going, she didn't even know where they were going.

“Um Dean? Where are we going?” Her sudden inquiry startled him out of the trace like stare he had on her.

“I told you, best place in town.” The cocky grin plastered on his face told her that asking again would be pointless. “Don't you worry your perfect little head, you'll love it, I promise.” 

They remained silent and content in the car for a few more minutes until they finally turned off into a residential area. Lisa had never been there, she didn't even know they had houses this far into the hills. All the homes they passed where grandiose and extravagant. She’d never seen anything like it before.

“Wow. These houses are huge! I didn't know there was anything out here, let alone restaurants.” Not quite realizing where they were headed yet, Dean watched her babble on about everything she was seeing.

The turn off to Dean’s property was at the very end of the lane, there was a ten-foot tall fence surrounding the whole thing, the only way in was through the massive security gate at the bottom of the road. The driveway was so long Lisa could barely see the front door from the car. He likes his privacy.

“Wait… this isn't a restaurant. Dean? Is this your house?” Finally understanding, Lisa was shocked and couldn't believe that anyone could live in this large of a home.

“Yep! I've got the best chef in town.” He felt a certain pride in knowing how amazed his new friend was with his place, and she hadn't even seen inside yet. Tuning out her newest babbling, Dean realized that Lisa honestly had no idea who he was or what he did. He liked that. He would be able to introduce her to a whole new world from scratch.

Driving up to the house from the gate took a few minutes, in that small amount of time Lisa never stopped talking, Dean could tell it was nerves. He assumed she was once again feeling inadequate.

“Welcome home!” Laughing at his own joke as he got out of the vehicle, Dean raced around the car to be a gentleman and open the door for his woman.

The house truly was magnificent. Sandstone covered the outside, beautiful bright flowers were precariously littered throughout the property, and the wrap around driveway led to a three car garage just off to the left of the main property. 

“Oh my goodness, Dean. This is beautiful.”

Dean had never had such a big smile on his face. His ego was being stroked and he liked it. He was loving every minute of this.  
“Come on baby, i’ll give you the tour.” His confidence was evident.

The grand tour consisted of of the master bedroom, four guest bedrooms, exercise room, movie room, living room, library, back yard, dining room, and it ended in the kitchen. Purposely avoiding the basement and the home office was Deans attempt to not scare Lisa before their supper.

“Alright, lets get cooking!” Dean hadn't told his date that they were the ones making supper, he just loved seeing a surprised look on her face.

“Wait, we’re cooking? I didn’t know you could cook.”

“I said I had the best chef in town.” Adding a wink just to make her blush. “How about we start with a drink?” Dean hadn't forgot about their previous date, at the Hell Hole, when Lisa told him she didn't drink. He hoped to be able to talk her into a glass of wine at least.

“I don't drink alcohol, Dean.” Lisa had this conversation a thousand time before, it seemed. 

“And why is that?” Dean questioned, still holding out hope to get her a little tipsy.

“I don't know, I just don't want to not be in control of what I'm doing, I guess.” That was a half truth, in reality, Lisa was petrified to get drunk. The thought of not being able to help herself if something were to happen made her terrified. It just wasn't worth it.

“Some people like losing control.” Deans voice was rough and a little strained, blood rushed down to his crotch as he pictured what she might be like drunk and helpless. Forcing himself to turn away, Dean once again willed away an untimely erection.

That was the most fun Dean has had in a a long time. They spent an hour dancing around the kitchen like fools while listening to music and cooking, well Dean cooked and Lisa chopped and stirred. Their faces ached by the time they were done from laughing and smiling so much. Neither wanted it to be over.

“Wow Dean, this looks amazing! Spaghetti is my favourite.” Lisa was partially lying, she didn’t really like spaghetti, but they worked so hard and Dean was being such a gracious host so she figured whats the harm in a little white lie.

'Did she just lie to me?' Dean thought to himself. He knew something was off the second Lisa had spoken. He could tell right away that she was a terrible liar. 'Perfect.' It was like she was made just for him. Hearing her lie to him for the first time made Dean curious, why would she lie about such a small meaningless thing like spaghetti, and what else would she lie to him about. He didn’t want to call her out for it though, Dean liked having the upper hand whenever he could.

Lisa was so concentrated on making sure she didn't spill any supper on her dress that before she knew it she was done her meal and had yet to say two words to her dinner date. She also missed the fact that Dean spent more time watching her than he did eating his own food.

“Oh my goodness, I didn't realize I was so hungry, I must look like such a pig.” Lisa was suddenly embarrassed when she looked up and saw that Dean still had half a plate left. She was growing tired of embarrassing herself in front of this devilishly handsome man.

“Nonsense. I'm done anyways, gotta save room for desert.” Deans toothy grin and smooth innuendos usually had girls begging to be taken to his bed. But he was somewhat disappointed when Lisa just giggled and stood up to clear her dirty dishes. 

After a very short, mostly one sided, argument, Dean managed to convince Lisa that it would not be rude to leave the kitchen a mess with dirty dishes. Glancing at the clock, Dean saw that it was almost 9:00pm. His men would be arriving with all of the stuff from Lisa's apartment and minute now, he hadn't gotten a chance to tell her about her new living arrangements. Deciding that he wasn't in the mood for a real argument, he chose to lead her to the home theatre so she wouldn't see all of her belongings being marched through the front door.

“Dean, I work in the morning, I should probably be getting back home. It's a long drive from here.” 

“Oh come on, it's been such a good date so far, let's watch a movie. That’ll make it the perfect second first date.” They both chuckled at the joke.

“Ok ok maybe for a little while.” Lisa said, allowing herself to be pulled down into the extra large recliner beside Dean. There was enough room for two people to easily fit in one of the chairs so Lisa wasn't uncomfortable being so close to her date.

Dean was glad that he didn't have to force Lisa to stay and sit for the movie, he definitely would have and he would have enjoyed every second of it. But this felt like a win. He was winning a game that she didn't even know they were playing. When he grabbed her hand and pulled her down to the chair with him, he half expected a polite rejection, but once again she surprised him. Albeit, she scooted her little body as far away from him as she could, she was still close enough for Dean to feel the heat radiating off her. It took all his strength to not rip her dress off of her and take her right there. 

The movie was some boring romantic comedy, Dean was barely paying attention to the plot. He was too distracted by the warm body sitting just inches away from his own. She was so small compared to Deans large body of rugged muscle.

“I'm gonna grab a drink, want some pop?” Dean had his fingers crossed, praying she would say yes. 

“Yes please.” She responded with a smile not knowing that Dean was rejoicing, on the inside, about how easy she was making this.

Reaching into his pocket Dean pulled out a little bag of white powder. He made sure to add a little to her glass and stir it before he handed it to her. The white power that he slipped into her drink was something to make her fall asleep, he could tell she would not willingly stay the night, but she could hardly argue if she passed out and woke up in the morning.

“Here Darling.” Dean handed her the drugged beverage and sat back waiting for it to kick in. He watched as her eyes began to droop. She made a few measly comments about going home, but she never quite managed to stand up to leave. He knew she was out like a light when he put one arm around her shoulders and the other hand on her upper thigh and she didn't move. 

All sorts of devious and dark thoughts entered Deans mind, but in this one instance Dean Winchester could be a patient man. He would instead settle for a quick feel of her body as he carried her upstairs to their new shared bedroom.


	15. How morning after

Dean awoke to a quick knocking on the bedroom door. He rolled over and saw Lisa still fast asleep, thanks to the little package of white powder he slipped in her drink the night before. The knocking on the door continued so he sat up and looked at his cellphone. It was seven o’clock in the morning! He also saw that he had several missed calls, his phone was on silent, they were all from Sam.

When Dean got up out of bed he made the decision that if it was Sam knocking on the door he wouldn't be angry, but if it was anyone else he was going to punch them straight in the face. He could forgive his little brother for interrupting his first sleep with his new woman, but anyone else daring to do it was just unacceptable.

Opening the door Dean was pleased to see that it was in fact not Sammy. He looked the poor man in the eyes and hit him as hard as he could right in the jaw. Getting excited when he heard a pop and a crack, Dean quickly closed the door behind himself while covering the mans mouth with one hand.

“If you make one sound that wakes her up I will kill you right here. What do you want?” The poor man paled at his words and tried to fight back a sob as tears began to fall down his face.

“M-s-y-“ The punch had clearly dislocated the mans jaw and he could no longer tell Dean the reason for knocking on the door in the first place.

“Fucking useless.” Smiling on the inside, Dean turned to lock the bedroom door just incase Lisa woke up before he got back.

“Ok Sammy, I'm up” Dean spoke to his brother when he saw him standing at the bottom of the stairs by the front door “what was so impo-“ The words being cut off mid sentence when he saw a bloody and bruised man being pushed around the corner of the living room and out into the foyer.

“What the hell is this?” It wasn't normal for Sam to do something as reckless as bring “work” home, so Dean knew something was up. 

“I wanted to formally introduce you this guy and show you this.” Sam reached in his back pocket and pulled out a cellphone, tossing it to his brother he then grabbed the poor bloody man and pushed him to his knees in front of them.

Dean wasn't sure what he was looking at. Sam had handed him a random cellphone. Turning it on, he immediately knew what was happening. This man was one of the drunken bastards from Lisa's apartment yesterday, and the cellphone, that was full of pictures and videos of her, must have been his. They were all taken from the same angles, these men had placed cameras around her apartment. Dean was fuming. By the time he got to the video of her in the shower he was ready to kill all of them.

“Where are the others?” Dean asked through clenched teeth.

“Already downstairs. I left this guy out for dramatic affect.” Sam smirked knowing his big brother would be proud of his choice to take the other men downstairs.

“You know me so well, Sammy.” Grabbing the man in a bone crushing grip, Dean quite literally threw him down the stairs to the basement. 

“I want Darren outside my bedroom, tell him to come and get me when Lisa wakes up. Oh! And send Toby and Josh downstairs, I might need some help.” Talking louder than normal to be heard over the blubbering man at the bottom of the stairs, Dean gave his orders and then descended to the PlayRoom.

The basement was a sight to behold. Three men were handcuffed, blindfolded, and kneeling in the middle of the room. Dean was happy to see that they were relatively unharmed, he would be able to punish them accordingly. 

“Well well well, what do we have here?” Sauntering into the room with the confidence of a man who knew he was in complete control, Dean pulled the man he had thrown down the stairs in behind him.

Tossing the bleeding man onto the floor with his friends. Dean turned to Mark, the man Sam entrusted to guard the new prisoners. “You can leave.” Rudely waving Mark away without another word. “I said get out!” Dean yelled when his command wasn't followed fast enough.

Waiting for the two men he had requested to come downstairs, Dean slowly stalked around his victims, his mind was a flurry of ideas. All he had to do now was pick the perfect punishment for these people. They had taken something from him, his chance to be the first person to see Lisa’s body. They had taken something from his new woman, her innocence and safety. These men would pay dearly for their wrongdoings.

“Ah, there you are” Seeing Josh and Toby enter the room. “I want them all stripped and strapped to the beds.”

“Okay, Boss.” Both men replied in unison.

Dean chose to just stand back and watch as his new toys were moved and displayed how he saw fit. One was on all fours, two were on their backs, and the last man was on his stomach. The possibilities were endless. His excitement grew with each passing second. 

He was now standing at the foot of all the tables stroking his pyjama covered cock. It was all too much, if he didn't do something to one of them soon them he would just blow his load right there. Finally making a decision, Dean began to undress.

“I want you guys to understand why you're here. I want you to really comprehend the gravity of the situation.” Loving the way his words were making the men shake and attempt to speak through their gags, Dean continued. “You see, you had the unfortunate timing of being attracted to a woman that belongs to me.” He want happy about the confused looks they were sporting. “Lisa, you're neighbour. She is mine and you weren't very nice to her, so now I have the pleasure of giving you the same treatment.”

The confused and frightened men on the tables were now beginning to see what Dean was getting at. As they looked around the room and saw the wall covered in sex toys and the opposite was covered in torture devices they could guess the fate waiting for them.

Finally undressed, Deans hard cock was free to stand at attention. As he took a good look at the toys strapped down and waiting for him, Dean thought back to the last time that he had a man down here. There was nothing Dean Winchester liked better than taking control away from someone, Woman were good, but to take away a mans control went straight to Deans head. It made him feel powerful.

“What do you think Toby? I’ve always wanted to see a real life human centipede.” Toby knew his boss was just trying to mess with everyones head, but there was still a little part of him that wasn't sure if he would go through with it. Everyone knew the Winchesters were crazy.

“Yeah, you could make your own movie.” Playing along for his jobs sake, Toby definitely did not want to see a human centipede.

“Now that is a good idea!” Clapping his hands together. “I never even thought of that!” Dean was being completely serious, he had never considered doing his own version of that movie.

Knowing that he would not be able to go much longer without fucking something, Dean chose to take the one on his hands and knees. Slicking up his shaft with the smallest amount of spit, he made sure to use just enough to get in without injuring himself. Dean glided up to the man and, without warning or speaking, rammed his almost dry cock into the kneeling mans awaiting asshole. It hurt like hell for Dean but he relished the burn. Judging by the screams the recipient let out, it was even worse for him.

“Please! Please! Stop it. I’ll do anything. I’m sorry!” The kneeling man was begging, pleading for Dean to stop. At this point he would say anything for the pain to stop in his once virgin hole.

“Yeah just like that baby, I love it when you beg.” Dean was on cloud nine. He loved taking a straight mans virgin assholes, it made him feel more powerful than just a normal fuck.

Dean started off with a slow pace, his cock slid in and out of the abused hole with a steady rhythm. The feel of the pull and burn from the barely slick member was lessened when the man began to bleed. Looking down and watching his blood covered dick force its way inside, Dean decided to take some pictures of his own.

“Pass me my cell.” Dean practically moaned at the thought of being able to relive this moment in the future.

“No, no, no. Stop please!” The abused man was now babbling, saying anything he thought would help his situation.

Up to this point the other men in the room had been quiet. Too shocked and scared to do anything, but now upon realizing how sick and twisted this Dean was, they started yelling and trying to free themselves.

“You sick fuck!”

“I’ll kill you for this!”

“You’re a dead man!”

The string of curses were promptly ignored. Dean was too interested in the orgasm he was chasing. Josh and Toby on the other hand, felt bad for the poor men but knew that once you crossed a Winchester you were in for a horrible death.

“These are going to make some good background pics.” Dean teased and taunted the man while he took pictures and a small video of the punishment he was dispensing.

After a while Dean felt an impending orgasm approaching. Not wanting this to be over so soon he decided he was finished with this man and wanted to fuck another one. First he had to finish teaching this one a lesson. 

So he stopped his assault and walked over to the wall on the right. Picking up his favourite carving knife, Dean twirled it around elaborately to get the attention of the victims. When they all got a good look at what he had in his hands, Dean walked back over to the man kneeling on the table and started carving his name in the poor guys back. His renewed screaming and begging only served to spur on Deans excitement.

“Wow. Look at that. Mmm. You look so good I almost want to take you again.” The winchesters loved their mind games.

“P-p-lease. I ca-can-t” The man was about to pass out.

“Oh no, I cant have you passing out and missing all the funny baby! I want to make sure you get to see me when I kill you.” Dean harsh words made the mans blood run cold. 

Dean wanted to watch the man die. That was always his favourite part. So he stalked around to the front of the man. Taking his blood covered knife in one hand and grabbing the almost dead mans hair in the other hand, Dean forced their eyes to meet. Sending a wink and an air kiss down to the victim, Dean sliced his throat with no final words.

“Alright. Who's next?” Chuckling at the terror he had caused the prisoners. “You?” Dean pointed at the man to his immediate right. “Don’t look so glum, my cock will be wetter for you, we’ll use his blood. How does that sound?” Sending an evil grin around the room, Dean went to slick himself up.

The door to the PlayRoom opened just as Dean was about to coat his dick in the dead mans blood. Everyone turned their heads at once. The men strapped to the tables took the opportunity to call for help, not realizing it was one of Deans men. 

“Uh sir? You wanted me to come and get you if she woke up?” Darren had run downstairs to fetch Dean when Lisa had woken up. He was slightly scared, not knowing how his interruption would be taken.

“Ah yes, terrible timing but my lady awaits.” Unusually chipper, Dean was almost excited to stop fucking with these men and go back upstairs.

Returning to the front of the room beside Josh and Toby, Dean turned to the men. “Gun” he commanded and held out his wait waiting. Rushing to obey, they each produced a small handgun. Taking the weapon from Toby, Dean sauntered to the first man in the line up of tables.

“Sorry we don’t get to play anymore. I have something more important to do.” Not leaving room for a response Dean shot the temple.

“You don't have to do this! Please!” The second man was crying so hard he could barely be understood. Sick of his whining already Dean shot him too.

“And last but not least. I really wanted to hurt you, baby.” Deans words were directed at the bloody and bruised man he had pushed down the stairs less than an hour ago. He was the final victim alive and Dean especially wanted to make him pay for the pictures and videos on the cell phone. 

“You’ll rot in hell for this! You sick bastard!” Resigned to his fate, the man chose to get his final words in before Dean killed him too. 

With a final smirk Dean grabbed the mans face and made sure to stare into his eyes when he stabbed the forgotten knife into the mans heart. 

“Alright boys. Clean this up, I have a date with an angel.”


	16. Her Morning After

The sun shinning through the large open window of the master bedroom was what eventually woke Lisa. It took her a while to really comprehend where she was. The room was foreign, it was not the small cramped bedroom of her apartment building that it should have been. Instead, when she sat up, she could see that this was a large expensively decorated bedroom with a small couch and chair in front of a wall mounted TV, and huge windows that were open to show an amazing view of the valley.

“What the …” Lisa's voice trailed off as she looked around, recognizing the room from Deans tour yesterday. “Hello? Dean?” She called out from her spot on the bed, hoping Dean was within earshot with a good excuse for her current situation.

Being half asleep from the drugs she was given the previous night, Lisa was slow-moving and confused. Getting up off the bed and stumbling around Lisa looked for her cell phone. She was unsuccessful. It eventually occurred to her that she should leave and look for Dean or a ride home. 

She staggered to the first door to her left, it was the bathroom, there was no way out from there. So she slowly made her way over to the next door. Pulling on the handle was useless, it was latched from the other side. Banging on the door and yelling out, Lisa was sure she had heard footsteps running down the hallway. Her shouts were ignored.

“Hello! Help! I’m locked in here!” Lisa was growing increasingly tired, she had to lay back down before she fell asleep standing up.

The woman barely made it to the bed before she was passed out. Her body only half under the covers. She fell into a deep dreamless sleep.

Overwhelming tiredness and the absolute confusion of her morning had Lisa so preoccupied, she never had a chance to notice her clothing. She was no longer in the dress she had chosen to wear for her date the night before. Dean had all of her clothing brought over, but he still chose to dress his new woman in one of his old t-shirts and a pair of his pyjama pants. He thought there was something absolutely adorable about the way she looked like she was swimming in them.

As tempting as it was Dean had barely touched her, besides when he carried her upstairs to bed. Sure he had taken in as much as his eyes would allow, her body was a piece of art, but he only touched enough of her to change her clothing.

There was a slight knock on the outside of the door. Dean had no intentions of stopping if he was told not to enter, it was his house after all. But he felt like being polite today.

“Hello baby.” His words fell on deaf ears as he entered the bedroom. “Well fuck.” Speaking to himself now he saw that Lisa was still asleep.

Sending off a quick text to Darren, scolding him for lying and making him rush what he was doing downstairs for no reason.

DEAN: wtf? She's still sleeping!

DARREN: She was banging on the door and yelling

DARREN: I swear!

Dean wasn't too upset, not really. He had rushed in the PlayRoom, but now that he was standing here looking at Lisa on the bed wearing his clothes, he was so head over heels for her there was nothing he would rather be doing. He could watch her sleep forever.

Carefully pushing her over to the middle of the bed, Dean scooted in behind her. Laying himself flat he turned her over slightly so she was cuddling his chest. This is how he wanted her to wake up, in his arms.

It was about an hour later before Lisa began to stir. Dean kept her nestled into him, but could tell she was waking up when she began to mumble words in her sleep. At first it had startled Dean. He had been busy rewatching the videos he had taken earlier. But now he thought it was just another of the many cute traits she possessed. 

“Lisa, Lisa? Time to wake up.” Dean said, growing impatient. He wanted to hear her voice again.

Watching her wake up was magical. She burrowed further into Deans chest and mumbling something about the sunlight. Slowly she began to come to her senses. 

Realizing that she was lying on something hard and not pillow-like, she looked up into the eyes of her admirer. 

“Oh my goodness!” She sat up with a small shriek as a light blush began to form on her cheeks. 

“‘Morning Darling” Deans minty breath and chipper attitude told Lisa that he had been awake for a while. “Ready for breakfast?”

Lisa didn't remember waking up a short time ago. She looked around the room with renewed confusion. “Where are w-“ she began to question before she saw the window and recognized where they were. “Why are we in your bedroom?” The weirdness of her situation not quite sinking in.

“You fell asleep and I, being the gentleman that I am, didn't want to wake you.” Dean had to hold back a grin at the way she so easily accepted his words. Pushing the blankets off himself he stood from the bed and began to walk towards the door.

“Oh… right. Well thank you.” Lisa struggled underneath her side of the blankets but eventually untangles herself and got up. “Wait.” She finally saw they clothing she had been dressed in. “Did you… undress me?” Suddenly feeling wary. 

“You are a very heavy sleeper.” Dean chuckled.

“You can't just- You shouldn't have-“ Lisa was not at a loss for words. A man had taken her clothes off of her and touched her body enough to put new ones on. How had she not woken up?

“Babe. Look, you couldn't sleep in that pretty little dress of yours, and I didn't want to sleep beside someone naked! What was I supposed to do?” Dean lied to her face.

“Did you, you know, see anything?” Lisa vaguely gestured to her body, a crimson colour flooding her cheeks at the thought of someone seeing her naked while she slept.

“Of course not. Do you think I'm some sort of perv?” Dean gasped in fake offence, trying his hardest not to think about how much he really did get to see and the little bit he allowed himself to touch.

“No no! I'm sorry, that's not what I meant. I swear, Dean. Look, I should really be going. Thank you so much for everything.” Lisa was appalled by herself. She had somehow managed to be rude to this poor man again. She felt terrible for insinuating that he might have been the type of man to do something like that.

“Nonsense, you're not going anywhere, its breakfast time.” Brushing off her guilt and apology, Dean opened the door he was standing in front of and motioned for her to go first.

“No really, I have to work. I'm probably already late, and it'll take forever to get back to the other side of town.” Dean watched her ramble on and look around, presumably for her clothing and cellphone. He had taken both and until he could trust her, she wouldn't be getting either back until he said so.

“Lisa, stop. We’re going downstairs for breakfast.” Dean made sure to speak with authority and finality. He didn't want to frighten her, but she needed to know we was in charge. 

Shrinking in on herself at his words, Lisa felt like she was in irate child being spoken to by a parent. “Okay.” Thinking that she was already late so a little breakfast wouldn't hurt, she agreed. She didn't want Dean to be upset with her, he had been so nice to her up to now after all. 

“After you then.” Dean loved the rush he got from having his orders followed, but it was a whole other level to have Lisa follow them. She didn't even argue too much. He felt like he was on a high.


	17. She's not having it

Arriving at the kitchen Lisa observed that it was completely cleaned from the night before. Now there were various breakfast dishes scattered atop the large island in the middle of the room. It was clear that there was too much food for just two people.

“Did you make all this?” Lisa was sure that Dean had not. 

“Nope.” Dean purposely left his answer vague.

Ushering his guest over to the adjacent dining room, Dean made sure to seat her beside his usual spot at the head of the table. Not wanting to leave her alone for too long, in case she bolted, he quickly jogged back to the kitchen. What would she like to eat? Dean thought to himself. Unsure of her food preferences yet, Dean just grabbed a little of everything and threw it on both of their plates.

“Here you go, my dear.” Handing the much too full plate to the small woman, Dean laughed a bit when he saw her eyes bulge out at the sight of the food.

The atmosphere around the table was tense and uncomfortable. Dean didn’t like it, and worse, he didn’t know how to fix it. It was clear that Lisa didn’t want to be here but Dean was more upset over her lack of appetite than anything.

“Hows it taste?” Dean asked with a seductive eyebrow wiggle.

“Its delicious, but i’m not that hungry, I should really get going.” Lisa said in a rush and stood, attempting to leave the table.

Dean fixed her with a hard cold stare, using his deepest commanding voice he instructed her to sit and finish her food. She promptly obeyed, not wanting to upset her host. Thinking she must have offended him a few moments ago she made a show of eating and commenting on how good the food was.

“Good girl.” Dean teased eliciting no response.

Using his ‘boss voice’ didn't make the situation any less tense, but now she was at least eating. When she was about halfway finished she sat back and looked at Dean. Her stomach was bursting at the seams. Too full to even move, let alone finish her plate.

“Dean?” She carefully ventured. “I-I don't think I can finish al this food.” Peering up at Dean in quick glances, Lisa expected him to be upset again. He surprised her by smiling.

“Thats aright Darling.” Dean was happy to see how nervous she looked. He could really get used to this timid shy behaviour she was showing.

After assuring her that he really wasn't upset over the amount of leftover food, Dean took their plates to the kitchen and led Lisa back to the front foyer and staircase. She hadn't said anything else about leaving since their meal, he almost hoped she would try and run just so he could chase her down. The thought alone had his blood rushing to certain places.

“I have to get going now … I’m already late for work. Where are my things?” Lisa looked at Dean expectantly.

“I’ve already called and gave them your resignation, you don’t need a job anymore. Besides, you’re too good for that place.” Dean wasn’t sure how his words would be received.

“What?!” Disbelief evident in her shock. “Why would you do that? I need that job. Look Dean, I’m going to go.” Voicing her displeasure, she slowly began to back up towards the front door.

Snatching her arm before she got too far out of reach, Dean grabbed Lisa and pulled her in close to his body. “Look Darling, you don't need a job now that you're with me.” He stated, like it was obvious. “And watch the way you talk to me, got it?” 

Lisa was alarmed at his change in behaviour. She tried pulling her arm from his punishing grip. When she couldn't get herself free she panicked and started pushing and hitting with the other hand.

“Dean. I want to go. You’re scaring me! Let me go, please!” 

“If you don’t calm down and behave i’m going to have to put you in time out.” Keeping a calm composure that was opposite to Lisa’s hysteria, Dean tried to hide his delight. He was loving the way she was acting.

“You’re crazy. Let me go!” Showing no signs of calming down anytime soon, Lisa was using all her strength to free her arm and fight off Dean.

“I warned you.” He replied with a grin.

That was all the warning Lisa got before Dean picked her up and threw her over his shoulder. She was stunned from the sudden movement for only a moment. Quickly renewing her assault, she had more vigour now that she could use both hands. 

“Ah! Put me down!” Kicking and punching with all her strength.

Dean let the abuse continue while he marched them upstairs, keeping one hand firmly over her legs to avoid getting kicked in the face. Once at the top of the staircase he gave her a firm hard slap on the ass.

“Knock it off or I will put you over my knee right here and spank your ass raw.” The threat was enough to make Lisa freeze. Unsure if Dean would actually do that.

“Good girl.” He teased for the second time this morning, giving her ass a light pat. 

The walk back to their bedroom was quick. Lisa was too afraid to move, mentally berating herself for the predicament she was currently in. Dean on the other hand was imagining the way her ass would look beaten raw by his hand in fury of anger.

Walking into the bedroom Dean shut and locked the door behind them. He didn't want anyone coming in or going out. Setting Lisa down on her unsteady feet Dean abruptly turned and walked into the closet, ignoring her feeble protests.

Once in her feet Lisa bolted to the door, she pulled and pushed with all her strength, but she had heard the lock click behind them. Frustrated and confused she turned her back to the door and slumped against it.

“Dean? You're really scaring me, please let me out.” She called out to the man in the closet, but figured he would likely ignore her request.

“I'm sorry my Dear, I warned you. I was putting you in time out of you didn't behave yourself downstairs.” The lack of emotion in Deans statement was chilling. He wasn't playing around.

“Y-you can-t keep me- here.” Trying to look brave she walked towards Dean with her arms crossed, her stutters betrayed her.

She watched as he emerged from the closet in a new set of clothes. “I can and I will.” He said as calmly as if they were discussing the weather. “I was hoping we would be able to go for a swim in the pool this morning, but now you’ve gotten yourself in trouble. So, time out it is.” He spoke casually while walking towards her, noting the fearful expression on her face.

Lisa was afraid of Dean, his recent behaviour was the opposite of what she ad previously known him to be. The roughness, the man-handling, and the odd way he was talking like it was normal.

Dean approached her dressed in clean dark blue jeans and a plain black t-shirt that was so tight she could see, for the first time, how large and muscular he really was. Up until now, Lisa had been very intimidated by Deans apparent wealth and immense confidence, but now she found herself unnerved by his powerful build and presence.

“I have some work to do downstairs.” Dean explained. “You are to sit here and think about why you are in time out.” As Dean talked Lisa was slowly backing away from him, he stalked her step for step. 

When she had gone so far that her back hit the wall he leaned down and whispered in her ear. “Be thankful a time out is the only punishment you’re getting, I would love to put you over my knee until you beg me to stop.” Ending with a kiss to the top of her head, Dean turned without another word and left the room.

The click of the lock that followed Deans exit from the bedroom was the final straw for Lisa. 'He cant just keep me here!' She thought to herself. Taking a brief moment to be proud of the way she was handling this very weird situation, she thought back on her strange morning and realized that she had not gotten her cellphone back.

When Lisa had woken up this morning she looked for a way to escape, of course she was still too heavily drugged and does not remember doing that, so she once again set out looking around the room for a way out.

She checked the bathroom, it was magnificent. Almost everything was marble. It had the biggest Jacuzzi tub she had ever seen and the standup shower was to die for. There were his and hers sinks, a big window with the same view as the bedroom, and some pretty pricy artwork. But no way to escape.

Next she tried the only other door she hadn't been through in the bedroom, the closet door. The walk in closet was massive, Lisa noted that it must have been the size of her whole bedroom back at the apartment. As she walked around and looked at the shoes and clothes she got a funny feeling. Upon closer inspection she realized that half of the closet was covered in her clothes. Even the things that had been in the laundry basket waiting to be washed. 

“What the…” Her voice trailed off when she realized what she was seeing. She knew then and there that Dean was crazy.

Quickly throwing on a pair of her own clothes, yoga pants, a t-shirt, and sports bra incase she had to run or climb her way out, Lisa was more adamant now to get home. Going back into the bedroom she decided the only other option was the window.

The window in the bedroom was huge, it took up almost one whole wall. The view was gorgeous, you could see the whole way down the valley. Most of it opened to allow fresh air but it was up on the second floor so jumping out would be difficult. Directly underneath it was empty, there was nothing to land on. But seeing everything made Lisa come up with a plan.

Running around as fast as she could she started grabbing anything and everything she could think of that would be soft to land on, and threw it out the window into one big pile. She took all the blankets, towels, pillows, couch cushions, clothes (Deans expensive suits included), and she even tried the mattress but it was too heavy. By the time she was done there was a significant pile for her to jump on outside the window. It was still two stories below so she had to find something to help her down.

Making a rope of sorts with all of the belts and ties that she found in the closet she knotted them as best she could and secured them to the leg of the small couch that she had drug over to the window. With her ‘rope’, her height, and the pile to land on she felt ok to climb out. 

Carefully shimming off the window ledge and swinging down to the end of her line she let herself fall. When she landed she immediately rolled like she had see in the movies a thousand times. It was basically painless. She made it out.

Now that she was on the ground she had to keep moving. Looking around Lisa saw that the closest corner of the house was to her left, so that was the way she went. Rounding the corner she ran until she hit the driveway at the front of the house. She was so close to freedom she could taste it, until she remembered the front gate. 

Lisa never really had good luck in her life, she always figured it was just one of those things. But now as she ran down the side of the driveway, ducking behind every tree on the way, she saw that her luck had been saving up for this one moment. 

The front gate was sliding open. A car had pulled up on the outside and someone had reached out to punch in a code on the keypad, unknowingly giving Lisa her escape. All she had to do was wait for the car to drive by and then she could sneak out.

“Come on, come on.” Quietly muttering to herself. 

The car took forever, but finally it crossed the threshold of the property and sped up the driveway. Lisa bolted. She knew she had never run this fast before. Using all her concentration to not trip or stumble she managed to squeeze by the gate before it closed all the way. 

Foolishly risking one look back at the house had her gasping and made her heart skip a beat. She had not been as stealthy is she assumed, someone had seen her and now she was being chased. There was a lot of movement and shouting at the top of the driveway. Shock freezing her in place, she only turned to run away when Deans car crested the hill and came into view.


	18. His After

“How did this happen?!” Dean roared as he slammed him fists down on the steering wheel in front of him, making everyone in the car jump. 

“Dean… we have everyone across the city looking, we’ll find her” Sam cautiously spoke, hoping to calm his brother. 

“This shouldn’t have happened in the first place, there should always be someone at the front gate.” Deans anger was rolling off of him in waves.

“I’m sorry Dean, I didn’t even see her there…” Deans anger was indirectly Sam’s fault. It was his car that had opened the gate and let Lisa escape.

Dean had been downstairs in the living room on the phone, waiting for Sam to arrive. They had a few work related things to go over this morning. Usually meetings were conducted at the office, but Dean didn’t want to leave Lisa here alone too long on her first day.

It was amazing that no one had seen Lisa’s ‘Big Escape’. Of course the cameras out front had seen her go down the side of the driveway, but by the time everyone figured out what was going on she had snuck off the property and disappeared into the city. 

If it had been anyone except Sam in the car that let her out Dean would have killed them with his bare hands. But since it was his baby brother he might just smack him around a bit after they find her.

“You better find her, Sam.” The unspoken threat in Deans words were well understood. Sam knew Dean wouldn't kill him, but he was still afraid when his big brother spoke like that.

The car ride was tense and awkward, everyone on their phones communicating with various people in the city that were on the lookout for Deans runaway girl. They drove around aimlessly, checking the few places they thought she would go.

“Where the Hell would she have gone?” Deans rhetorical question went unanswered.

Just as he was about to start beating the steering wheel again, Sam’s cellphone rang.

“What.” He rudely answered, much like his brother when it came to manners. 

It was the police station nearest Deans home. One of the officers on their payroll had seen Lisa come in. He was holding her, just waiting on word from the boss.

Slamming on the brakes in the middle of the street Dean came inches from causing an accident. He jammed the car in reverse and sped back the way they had just come. Giving everyone minor whiplash. Dean was now hopeful and excited. He couldn't wait to show Lisa what happened when people went to the cops. She would be getting a real punishment this time, no more ‘Mr. NiceGuy’.

Pulling up to the station in record time, Dean parked out front and hopped out. Rushing over to Sam's side of the car he bent down to speak with his brother briefly.   
“I’m going in alone. Pull around back and keep the car running, just incase she decides to make a scene.” Sam jumped up to meet his big brothers instructions with immediate obedience.

Walking up the steps to the precinct Dean tried to settle the butterflies in his stomach. The relief of finding her so quick along with the knowledge of her impending punishment was making him giddy.

The gang had many people throughout the city on the take, cops included, so Dean could find his away around all of the precincts. Knowing exactly where he was going he marched in with the confidence of a man who had fucked most of the women, and a few men, he walked past. Ignoring all of the lustful look she was getting he headed for the elevator and went straight to the second floor. Dean was on a mission for Sergeant Parten’s office.

“Where is she?” Dean demanded from the sergeant that was nervously waiting outside the elevators for him.

“She’s- ah- she’s in my office, Mr. Winchester.” The poor man was shocked, not expecting Dean Winchester himself to be the man coming to collect the crying woman currently seated in his office.

“What has she told you?” Walking past the stuttering man and heading for his office, Dean wanted to know how foolish his new love actually was.

“Ah nothing Sir. I don’t think she actually knows anything. She's just scared and confused, she’s crying and just wants to go home.” Parten sounded confused himself. “I don’t think she even knows what you’re last name is.” He added as an after thought.

Dean silently listened to the man. The first thing his father thought him about the family business was to never say more than you have to when talking to the cops. But he was rather interested to hear that even after all hat has happened his little Lisa was still clueless.

“You did good. You will be thanked for this, now go away.” Dean stopped just outside the office door and spoke rudely to the man on his heels. 

“Yes, sir.” Sergeant Parten wasn't surprised by the tone or even the words that Dean had used, but he still felt uneasy about leaving that poor girl alone with this psychotic man. Seeing no other choice, he turned and walked away, praying there would not be a crime scene to clean up when he returned.


	19. Her After

Lisa didn't know where to go. She had no money, cellphone, or idea where she was. After escaping Deans house she ran until her lungs burned and her legs gave out. By the time she stopped to catch her breath she realized that she didn't know where she was. Lost, scared, and alone, Lisa went into the closest building and asked for directions to a police station. Her parents always told her to go to the police if she was ever scared or in trouble.

The walk to the closest station was short, thankfully she had run in the general direction of it earlier. Jogging up to the front door and hurrying to the reception. As she waited in line to talk to someone her eyes began to tear up, the stress of everything was beginning to finally weigh on her. The poor woman didn't even know why she was crying, everything just hit her at once.

Standing in line silently crying, Lisa didn't realize a man was staring at her. Well actually he was trying to compare her face to the picture of the woman on his cellphone. It was Searent Parten and he had just gotten a text from Sam Winchester telling him to keep an eye out for this young woman.

“Excuse me, Miss? Can I help you?” The Sergeant asked as he approached the woman. When she turned to face him upon hearing his words he knew right away this was the woman everyone was looking for. 

“I need to talk to a police officer.” She mumbled out between sniffles.

“I'm Sergeant Parten, how about you come with me to my office and I'll help you out.” Putting on his most sympathetic smile he quickly guided her to the elevators.  
Lisa should have noticed how unusual and unorthodox that was. But she was preoccupied in her mind trying to get her story straight. Not sure what it was she could even tell the police she was suddenly worried that there would be nothing they could do for her.

“Right this way, Miss…” The man directing her out of the elevators paused waiting for her name.

“Holland, Lisa Holland.” Slightly blushing from the intense look she was receiving from the older man, Lisa quickly stepped ahead of him so they could continue walking.

They silently walked around cubicles and passed by various desks. Finally they came to a standstill outside the sergeants office. He opened the door and gestured for the young woman to go ahead of him.

“I'm going to go get you some water. Have a seat, i’ll be right back.” His abrupt exit was not noticed.

Lisa took a look around the office, as she sat down. There were two black leather chairs facing a large and neatly organized desk. The desk was void of any pictures or sentimental ornaments. The walls were sparsely decorated with different awards and certificates.

“Here you go, dear.” The sergeant came back to the room a few minutes later and handed Lisa a paper cup filled with luke warm water. He had really only left to call the Winchesters and tell them he had found the girl. 

“Oh, thank you.” Lisa had mostly stopped crying by now.

“So, Lisa.” The man started off the conversation as he sat down behind the desk. “Tell me why you're here. What happened?”

Giving her statement took longer than she thought, Lisa didn't know where to start. She had been held against her will by a man that she was having dinner with the previous night. She couldn't even remember what he had said it last name was. The story sounded ridiculous, even to her.

“Well if thats all you can tell me… I’m going to go get a coffee, I’ll be right back.” Sergeant Parten was somewhat relieved, surely this girl couldn't be in too much trouble with The Devils. He made his second hasty exit and went out to the elevators to wait for someone to come get this young woman.

This time Lisa had noticed the Sergeants abrupt departure, she just figured it was an excuse to leave because he didn’t believe her story. She never thought in a million years that Dean Winchester would be the next person to walk through the door.

“Hey, Darling.” That silky smooth voice made her blood run cold.


	20. Punished

The room was tense, the air suddenly stale. Dean was the dangerous predator who just proved he would catch his prey no matter where she hid. Lisa was the helpless prey who was cornered with no where left to run.

Dean Winchester sauntered into the office with his never faltering confidence. Placing a hand on the side of Lisa’s cheek, he lovingly rubbed back and forth. When she tried to turn away he roughly grabbed her by the chin and forced her to face him.

“You've been a real bad girl, baby.” Dean enjoyed the way his words made her shiver in front of him.

“Dean… How did you find me here?” Lisa was too afraid to move, once again she was shocked into place.

“Nothing happens in this city that I don’t know about.” Dean whispered. “I own everyone.” He was exaggerating, but Lisa didn’t know that. 

The feeling of his strong calloused hand squeezing her small face brought her back to reality and helped the shock wear off. Now she was confused.  
“What do you want from me?” She asked.

“Darling, I already told you. I want all of you, and I always get what I want.” Dean was almost mad, how could she not see that she belonged to him. “You're mine.” He growled out and pulled her up to stand before of him.

“Please, this is a police station … I'll scream!” Lisa threatened, remembering where they were.

“Pffft. All the cops in this city work for me, how do you think I found you?” Dean rolled his eyes at her. “I'm tired of this. We are going home. You can be a good girl and walk with me, or I can throw you over my shoulder and carry you out.” Dean looked at her expectantly, waiting for her to choose.

Lisa's mind went back to earlier in the day. Dean had carried her up the stairs and smacked her ass the whole way. She didn't want him to touch her again. Not seeing a third option she quietly agreed to walk downstairs. 

Dean tried to not let his disappointment show. He knew she wouldn't have put up a fight, but he was still hoping he would get to hold her against him again. But he gave her a fair choice and she made the decision. If he wasn't consistent and true to his word then she wouldn't learn properly.

“Well ok then.” Grabbing her by the hand Dean led them out of the office and down the back staircase to his awaiting car. Opening the back door he told the two men in the backseat to get out. He shoved Lisa into the car and shuffled in behind her.

“Take us home, Sammy.” Dean never let his brother drive his favourite car, but today was clearly a day for exceptions.

Surprisingly the drive wasn't tense or awkward. Dean placed a hand across the car firmly on Lisa's knee, every once it a while when she would look over at him he would give a little squeeze without looking at her, just a gentle reminder of who was in charge.

Sam and Dean kept up a steady stream of small talk, some of it work related and some of it not. Neither acknowledged the trembling girl in the backseat. This was another mind game Dean liked to play and Sam knew it. The calm before the storm.

Pulling up to Deans property, Lisa could see that he now had two armed men guarding the front entrance . 'So much for that escape route' she thought to herself. She would have to make a new plan to get out next time.

“Home sweet home.” Dead commented as they pulled up the driveway.

When the car stopped Dean leaped up dragging Lisa behind him. Rushing through the front door he remained silent and pulled her back upstairs to the bedroom. Lisa put up a little fight, trying to tug her arm out of his grip when she saw she was being taken back upstairs.

“Dean… Please don’t do this.” Lisa half cried, finally breaking the silence as they ascended the staircase.

Dean chose to remain quiet and ignore her words, sometimes his victims would spiral out of their minds faster if he didn't answer back. That was always fun to watch. Finalizing the details of the way he was going to punish her took most of the walk from the stairs to the bedroom door.

“Get out.” Walking into the bedroom Dean was forced to break his silence when he saw that they weren't alone. His cleaners were putting his room back together after Lisa’s big escape. 

Slamming the door behind them, Dean snickered to himself when he felt Lisa jump from the loud bang. When he turned back around the room was deadly tense. Dean was waiting for Lisa to cry and beg. Neither made a move.

“Last time you got in trouble I went easy on you. Against my better judgement I gave you a timeout, instead of putting you over my knee.” Accenting his words with a menacing look, Dean approached Lisa and continued talking. “I won't make that mistake again. I've had plenty of time to think about your punishment. You're going to be sorry you were a bad girl.” His words having the desired affect when Lisa began to cry aloud.

He grabbed her by her small frame and pulled them towards the large king size bed. Sitting down on the edge he made sure to sit in a way that Lisa would fit draped across his legs. When he got seated comfortably he pulled Lisa down over his lap.

There was no denying the erection he was sporting, but for the moment it was ignored. Dean couldn't help but get turned on now that he finally had his hands all over his new lovers body. Her wiggling on his crotch with a tear stained face was really testing his will power.

Holding her down with one arm on her back, Dean tugged her pants and underwear down with the other hand. When she realized what he was doing she cried out and tried to sit up. She wasn't strong enough get away.

“W-what are you doing?” Even though it was currently happening to her, Lisa still couldn’t believe she was on a mans lap about to be spanked like an irate child.

“I’m going to spank you. You’re getting 50 with my hand. You will count every one of them. Am I understood?” Dean knew she wasn't listening to him. Smacking her ass to get her attention he asked her again. “Am I understand?” 

“Dean… Please don't do this!” Her crying intensified when he rubbed small circles into the spot he had just spanked.

“I’ll say it one more time baby. You're going to take your punishment like a good girl, and you’re going to count them out. Ok?” Dean grabbed Lisa by the hair and turned her head to face him, making eye contact while talking to make sure she heard him this time.

“P-please.” Was all she managed to stutter out.

They both knew that a punishment was going to happen regardless of how much begging was done, so Lisa eventually stilled her movements and tensed up in anticipation of the first hit. She was surprised by the strength behind the first blow and cried out as Dean brought his strong rough hand down on her soft smooth bottom.

“Count.” Dean barked. 

A barely audible “One” was heard between cries so Dean continued. His harsh assault of her backside seemed never ending. He knew the best way to inflict a punishment was to keep them guessing, he alternated between slow hard smacks and a series of rapid stinging slaps.

By the end of the punishment Lisa was barely coherent, the panic and pain had taken over her body. Crying more than counting, she somehow managed to finish her counting alongside every hit. Dean was impressed, she had taken her first real punishment very well. 

“Good girl.” Dean coo’d and teased. She had taken everything better than he expected. In an attempt to sooth and comfort her he lightly rubbed tiny circles over her bruised and beaten skin. It was painful and he enjoyed watching her wince and flinch every time his hand went over a particularly bad spot.


	21. Re-written First Time

**Summary for the Chapter:**

> I hated the way the last one was written, this isn't any better but oh well.

Dean had been very good since he sat down, he understood that this was about Lisa being punished for disobeying. But now that it was over and he was winding down from the excitement he couldn't help but notice that her naked ass was in his hands. She was pinned down and too hurt to fight back, not that she could overpower him at her full strength anyways. 

“Mmmm. You look so good with my hand prints on you.” Deans words were having the duel affect of turning him on and scaring her. “You should never wear clothes. It’s a shame to hide this perfect little ass.” As Dean talked he began to kneed the sore flesh in his hands, he relished in the pained moans she let slip out.

Lisa’s mind was having a hard time catching up to Dean. She was in pain and confused. The groping and weird words were making her uncomfortable. “Please, don’t.” Was all she dared speak at the moment. Not sure what he was planning next, she silently prayed that the punishment was over and he would just leave her alone.

“Come on baby, let Daddy see what you're trying to hide.” Talking more to himself at this point, Dean reached over with the hand that was holding Lisa down and spread her ass cheeks apart. His breath almost caught at the sight. It was perfect. Her untouched rosy pink holes were on full display for him.

Lisa was unable to sit up or help herself, so instead she just shoved her beet red face into the plush blanket underneath her. No one had ever seen that part of her body. And now there was a man so close to it that she could feel his breath on her delicate skin.

Bending down to blow a puff of cold air onto her most innocent spot, Dean was pleased to see her quiver and twitch. He observed that her face was hidden and her shoulders were slightly moving, she was crying soundlessly into the duvet. It was a sight he wanted to see everyday for the rest of his life.

“You were such a good girl for me, Lisa. I think you've earned a reward. What do you say? Want Daddy to make you feel good?” 

Dean wasn't about to stop, even if Lisa suddenly spoke up and declined his very generous offer. His mouth was salivating at the picture before him. Not waiting for a response he quickly slid his thumb into his mouth and wet the pad of it with his tongue. 

“Its been a while since I’ve been with a little girl like you, and I guarantee you’ve never been with a man like me.” Once again speaking more to himself than the woman in front of him.

Pulling his thumb from his mouth Dean slowly brought it down to the heated flesh of the crying girl in his lap. Tracing the outline of her slit as lightly as he could, Dean was waiting for a response. He knew he had beaten the fight out of the woman, but he still wanted to hear her meek protests. The begging was always Deans favourite part.

“S-s-stop. Please. I’ve never do-done this before… please just let me go.” As expected Lisa finally spoke up and voiced her displeasure. 

Something in the way she spoke made Dean pause. He was good at reading people. It was obvious to him that she was inexperienced and he knew for a fact that she had never had a boyfriend, but it had suddenly dawned on him that she has a virgin. He had the finest piece of untouched skin in the whole city naked and crying in his lap. His dick had never been harder.

“Oh my God. Are you a virgin, baby?” Grabbing a fist full of her hair and turning her to face him as he spoke. “How have you managed to run around my city looking like a piece of jail bait and not get yourself fucked?” The questions were obviously rhetorical so Lisa just silently cried while he talked.

While Dean was in awe of the new found information, he was all of a sudden even more turned on. As impossible as that seemed. 

“I’m going to fuck you, Lisa. I’m going to be the first and only cock you’ll ever have inside you.” His rough voice accentuating the urgency of his lust.

Now that Dean knew about the untouched body in his hands he made it his mission to at least get her wet before fucking her. With his newfound goal in mind, Dean began rubbing her again. 

Sliding his wet thumb up and down her slit, he was being as gentle as he could be. Slowly Dean inserted the finger and moaned aloud as the tight heat enveloped it. He thrust his thumb in and out a few times before switching to his, better suited for the job, middle finger.

“…stop.” Lisa’s voice was so small and muffled, if Dean hadn’t been listening for her cries then he surely would have missed it.

“Mmmm. ” Was all the acknowledgement she received.

Dean used his thumb to rub her clit in slow small circles. “Can’t wait to fuck you. You want Daddy’s big cock don’t you, I’m going to be nice and get you wet first.” He kept up his slow ministrations until he felt her unconsciously relax in his arms.

Lisa began to cry in earnest when Dean stopped rubbing her clit to add another finger. She felt her vagina stretching around something for the first time in her life. It was uncomfortable and she didn’t want it, but slowly as he worked them inside her she felt herself starting to open. He scissored his fingers a few times then took them out to spit on them before shoving them roughly back inside her.

When Dean felt her pussy start to respond to his hands and become wet on its own he stood up to rearrange them. He moved her so she was lying on her back up in the middle of the plush bed. Standing and looking down at the poor girl was something else, she was flushed red from head to toe. The perfect little virgin.

Grabbing her forgotten pants that were previously pushed down to her ankles, Dean made quick work of undressing her. Pulling her shirt and bra off was a little bit more of a struggle, but those too were quickly removed.

“Look at me!” Deans loud voice startled Lisa and she rushed to follow the order. He wanted to see her face when she saw his hard cock standing at full attention for her. Dean removed his clothes but took his time revealing his crotch. As he slowly pulled his underwear down he felt his cock spring up and slap his stomach. The fear on Lisa’s face at the size of him served to fuel his desire.

Climbing onto the bed Dean slowly kissed his way up Lisa’s body, stopping to spread her thighs and roughly mouth at her pussy. She gasped and immediately reached down to push his head away, but Dean was too strong.

“I like when you try to fight me.” She felt the words and accompanied smirk on her hot flesh.

Making quiet hurt noises when his scruffy beard got to be too much for her delicate skin, Lisa almost sobbed in relief when he lifted his face to speak. 

“You taste so good baby.” Deans mouth was covered in a mix of Lisa’s juices and his own saliva. Her body was responding to his torments without her consent. Lisa felt goosebumps break out across her naked body and her nipples hardened as a shiver ran down her spine. In any other circumstances she would almost enjoy the things being done to her body, but here in this room with this man she was scared and just wanted it to stop.

Dean was slowly humping the bed beneath him, rubbing his cock on the satin blankets was enough to hold off his need to be inside her, for the moment. 

“I’ll stop when you come, baby. I can feel your body shaking, I know you’re close. Cum for Daddy and this will all be over.” 

Lisa was surprised by his words, she had never had an orgasm before and she didn’t think she could with Dean, but her body was enjoying his experienced mouth and hands. She didn’t think she could hold off for too much longer.

Dean reached up with his left hand hand began to pick and flick to her swollen nipples, he had felt her body shiver and knew her nipples would be hard and sensitive. Growling into her mound when she squirmed away from his hands on her breasts made Lisa still again. She now moaned and whined as his mouth sucked her clit and his hand abused her nipples. 

“Ohhh, please, its too much!” Lisa cried out at one particularly hard pull of her sensitive skin.

Sensing that she was close, Dean replaced his fingers back into her soaking wet pussy. Setting a hard and rough pace he made sure to run his fingers over her G-spot with her pass. She was falling apart in his hands and it was beautiful.

“W-w-wait, stop. Dean, please, I feel like I’m going to…” Lisa never got to finish her sentence as her body spasmed and twitched in his hands. She was held still through her first orgasm and only when she stopped moving did he let her go. 

Dean sat up and looked her over without a word. She was beautiful lying on his bed, breathing hard, with a pink blush running from her ears to her toes. He had tasted her on his tongue and now he would feel her on his cock. 

“I’m going to fuck you now, Lisa. Its going to hurt, but I want you to remember this.” Using the smallest amount of spit to slick up his member, not that he needed it with how wet she was. Dean moved up the bed until they were eye to eye and lined up his throbbing manhood with her wet hole. When she finally looked him in the eyes he thrust all the way into her small abused body. He mercifully stilled and gave her a moment to adjust to the new sensation.

Lisa cried out, she had never known this type of feeling before. He was far bigger than the two fingers she had been stretched with. Having Deans large body over shadowing hers and harshly pushing her into the bed made her feel claustrophobic and trapped. She pushed with all her strength at his chest and began to beat him with her fists.

“God you’re amazing! I love when you cry and fight me, just makes me want to fuck you harder!” As Dean spoke he set a punishing pace and fucked into Lisa hard and fast.

It was all too much. The spanking foreplay, discovering her virginity, and then eating her out until she came all over his face had Dean sprung and ready to blow already. Reaching down to hitch her leg up, almost bending her in half, he began biting and marking his territory wherever he could reach. Dean found a particularly sensitive spot on her neck and sucked until he had the copper taste of blood on his tongue. 

“Look at me, baby. I want to see those pretty eyes when I come in you for the first time.” Without slowing his brutal thrusting Dean was able to turn her head to face him again. 

With a bruising grip on her chin he felt his release approaching. He didn’t want it to be over so quick, but he couldn’t help it. Deans hips snapped back and forth for a few more minutes before he finally stilled and felt himself coming deep inside her body. He allowed himself to slowly fuck his cum into her trembling body as he captured her mouth in an almost romantic kiss.

“Fuck. I don’t think I’ve ever come that fast before. You’re too good, baby.” As Dean spoke he carefully removed his softening cock and moved both of them so he was spooning Lisa from behind, underneath the blankets.

Mental and physical exhaustion quickly pulled Lisa into a deep sleep and Dean was able to lay back and think over what had just happened. He had found the perfect woman, she was quiet, submissive, naive, trusting, and absolutely gorgeous. ‘I am never letting you go’ he thought to himself as he leaned forward and nuzzled into her fiery hair.


	22. Happy Dean

Dean didn’t mean to fall asleep cuddling his new prize, but he was startled awake hours later when Sam had come to discuss some unfinished business. Swearing and stretching as he sat up, Dean briefly forgot about the sleeping woman beside him and called for Sam to enter the room. Patiently waiting in bed while Sam used his key to unlock the door from the outside.

“Hey Dean, sorry for interrupting your …. Wait, are you spooning?” It was unusual for anyone to see Dean doing anything remotely romantic, let alone spooning in his own bed.

“Shut up Sammy.” With no trace of anger in his words, it was obvious to Sam that Dean was relaxed and happy, probably from some mind-blowing sex with the poor girl he had seen earlier that day.

“Whatever, I’m going back downstairs, get dressed and come meet me in your office.” With a chuckle Sam left.

Dean doesn’t let anyone tell him what to do, but when he’s in a good mood Sam can pretty much get away with anything. Deciding that he was too hungry to stay in bed any longer anyway, Dean got up out of bed and began to redress himself, sneaking small glances towards Lisa. She had woken up when he called for Sam to open the door, and now was sitting up watching Dean silently move around the room. 

“I have a meeting downstairs. If you get out of this bed for any reason other than to use the bathroom you will be sorry. Do you understand me?” When he was fully dressed Dean stopped at the foot of the bed and levelled Lisa with a stare that made chills run down her spine. “Tell me that you understand.”

“I-I understand.” Lisa was afraid to argue, her pervious punishment making it hard for her sit on her bottom without constant shifting and wincing.

“I’ll have your supper brought up. If you’re a good girl and stay put then I have a surprise for you, if not I’ll spank your ass raw and believe me when I say I’ll enjoy every second of it.” He started to get a slight erection to the mental picture so he quickly turned to leave, having no time to fuck her right now.

“Can… can I get my clothes?” Lisa asked, her voice barely above a whisper. Clearly she didn’t want to keep Dean in the room for any longer than she had to.

“No.” Dean replied after only a second of thought.

Dean was incredibly territorial and admittedly jealous, he didn’t want anyone to see his innocent little Lisa’s perfect naked body, but this was part of her punishment. He knew that she would be mortified to be denied clothes in a house full of big scary men that could come into the room at any moment, Dean would never allow anyone to touch her but of course she didn’t know that yet.

The news of her prolonged nudity was upsetting and Dean was pleased see a fresh set of tears form in her eyes but was surprised to not hear a complaint or cry. Deciding that the conversation was over he left the bedroom and closed the door behind him.

Out in the hallway he sent a text to Darren telling him to bring super for Lisa and stand guard outside the door. Dean was confident that Lisa wouldn’t disobey him this time, but even if she did manage to escape the house she would not be able to get passed the new security guard at the front gate.

Dean was satisfied that Lisa would be taken care of while he was gone and left in search of a quick bite to eat. He went downstairs to the kitchen hoping to find leftovers of the meal he had made with Lisa less than a full 24 hours ago. It felt like years ago.

“Thought you were going to my office?” Dean was somewhat startled when he walked into his kitchen to find Sam sitting at the counter with an untouched plate of food and a bottle of beer in front of him.

“Right, cause I don’t know you. I don’t know that you’re like a starving dog after you fuck.” As Sam spoke he pushed the food and beer across the counter towards his brother.

“Fine little brother, you got me. I was coming to eat before I got back to business. So what was so important you had to interrupt the best post sex nap I have ever taken?” Dean Picked up the offered food and turned to leave the room, not stopping talking, knowing Sam would follow. “I have to say though, Sammy. I like the look of you in the kitchen having food ready for me.” Throwing a smirk over his shoulder, Dean inwardly laughed at the bitch face Sam shot back at him.

The men walked quickly to Deans home office, leaving all jokes and banter at the door. The office was a place for serious issues, and if Sam wanted to talk business in here then it was more important than the usual day to day job.

“Okay, Sammy. Whats up?”

“Well its nothing too important actually, I just wanted to go over the new security details you had put in place for your house. Away from anyone else incase there was something special you wanted” Sam was trying to speak as casual as he could, knowing Dean wouldn’t want to be reminded of Lisa’s earlier escape made this a dangerous conversation.

“I told you what I wanted. Two guards at the gate, more cameras out back, and a tracker for Lisa. Its not that hard to understand, why isn’t it done yet?” Dean was still on a high from his sex session and was trying to not let his impatience come out. 

“It is Dean!” Sam was quick to reply. “The tracker is being made as we speak, but I just wanted to double check that you didn’t want anything else done.” 

“No, I’m going to keep her on a pretty short leash. I don’t think she’ll be getting another opportunity to … lets call it ‘go for a run’.” Chuckling out loud like he just made a joke, Dean decided the conversation was over and dug into his food.

Sam knew from previous experience that Dean’s good moods never lasted so you should enjoy them when you can. He chose to stay and chat with Dean while he ate, basking in the smiles and lighthearted conversation Dean sent his way.

Dean loved spending alone time with his brother, in fact, it was his favourite thing to do. He was always content to just go for a drive or watch an old movie and binge on some junk food. Today would have been the perfect day for them to just lounge around the house, but Dean couldn’t stop thinking about Lisa.

His mind kept wandering off to what she looked like crying in his bed when he left. Had she been good and stayed put? Was she just sitting there in fear, or had she turned on the TV? Maybe she conned Darren into a conversation. That seems unlikely, he had left her fucked out and naked in bed. After a moments thought he decided she was probably sitting in bed with blankets up to her neck eating supper.

“Well this was fun, thanks for the food, Sammy. But I have unfinished business upstairs. Got the phone?” Dean spoke as he finished the last bits of his supper.

“Oh, yeah. Here.” Sam quickly pulled a cell phone from his pocket and handed it to his brother. “Its all set up the way you wanted. I kept the old one, wasn’t sure what you wanted done with it.” 

Dean grinned, Sam was always so afraid to do anything without Dean’s permission first. “Destroy it, we wont be needing it anymore.” With that, Dean stood up from his spot across from his brother.

“Wait… uh, do you maybe want to watch a movie or something … later?” Sam was unsure how the request would go, but the last hour of brotherly bonding had him wishing for more.

“Sorry Sammy, gotta get back. Maybe tomorrow the three of us can watch that chick flick you’ve been whining about.” 

Sam’s cheeks burned with the teasing, but it was obviously the closest thing to a ‘yes’ that he was going to get so he just smiled and said “Okay”.

Leaving his dirty dishes for someone else to clean, Dean went to the kitchen to grab a beer before he made his way back upstairs. He walked slowly and let himself enjoy the satisfied feeling deep in his gut. He could really get used to this.


	23. Meanwhile

*Meanwhile*

She wasn’t all that surprised. When she gathered the courage to blurt out the request for her clothes back Lisa knew that there was a very good chance that she would be denied. She of course was and was forced to sit in a strange mans bed naked trying to fight off a new onslaught of tears.

Watching Dean leave the room was a comfort and Lisa was finally able to release a breath she didn’t realize she had been holding. The sound of the door locking from the outside hadn’t gone unnoticed. Considering all that had happened in the past day it was the least of the poor girls worries. 

After a few steadying breaths and a moment of peace and quiet Lisa allowed herself to stretch out in the bed and take stock of her body. Dean had raped her. He had taken something from her, an innocent part of herself that she had guarded for twenty years. Nothing felt different though, that was what shocked Lisa the most. Her lower body was a little sore like he said she would be and she was sticky from things she didn’t want to think about but all-in-all she was fine.

Calming down was easy now that Lisa had verified that she wasn’t too injured. Finally sitting back up Lisa took a look around the room. Her cell phone was still no where to be seen and her clothes were too far to reach without getting off the bed. It was clearly part of her punishment to sit in bed like she was.

It only took a little bit of shuffling around for Lisa to get one of the bed sheets untucked and wrapped around herself so she could scurry to the bathroom. She locked the door once inside, even though she got the feeling that nothing would stop Dean if he wanted in there.

After quickly relieving herself she took a second to look in the mirror. Her face was tear stained and when she opened the sheet there were bites and bruises across her body. If the circumstances were different she would almost giggle at having her first hickey.

The varying emotions and well earned exhaustion of the last days trauma was finally beginning to set in so Lisa pulled herself away from the privacy of the bathroom and trudged slowly back out to the main bedroom. 

She was surprised to see that there was now a small tray of food and a large glass off water on the bedside table, she had not heard the door open or close. There was a little bowl of soup, half a club sandwich, and a large glass of water. The soup smelled exquisite, it was clearly homemade but Lisa had no appetite.

Deciding that it wouldn’t make sense for Dean to poison her now, Lisa took a drink of the water and crawled back into the bed. She was asleep within minutes.


End file.
